Developments in the Chemical Synthesis of Heparin and Heparan Sulfate

Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure‐to‐biological f...

Celý popis

Uloženo v:

Podrobná bibliografie
Vydáno v:	Chemical record Ročník 21; číslo 11; s. 3238 - 3255
Hlavní autoři:	Pongener, Imlirenla, O'Shea, Conor, Wootton, Hannah, Watkinson, Michael, Miller, Gavin J.
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	United States Wiley Subscription Services, Inc 01.11.2021
Témata:	Carbohydrates Chemical Phenomena Chemical synthesis Construction glycosaminoglycan Glycosaminoglycans glycosylation Heparan sulfate Heparin Heparitin Sulfate Oligosaccharides Structure-function relationships Sugar Sulfates Sulfation carbohydrates heparin glycosylation heparan sulfate glycosaminoglycan
ISSN:	1527-8999, 1528-0691, 1528-0691
On-line přístup:	Získat plný text
Tagy:	Přidat tag Žádné tagy, Buďte první, kdo vytvoří štítek k tomuto záznamu!

Abstract	Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure‐to‐biological function axis. In this review we focus on chemical approaches to and methodology improvements for the synthesis of these essential sugars (from 2015 onwards). We first consider advances in accessing the heparin‐derived pentasaccharide anticoagulant fondaparinux. This is followed by heparan sulfate targets, including key building block synthesis, oligosaccharide construction and chemical sulfation techniques. We end with a consideration of technological improvements to traditional, solution‐phase synthesis approaches that are increasingly being utilised. This review describes recent advances (2015 onwards) surrounding the chemical synthesis of heparin and heparan sulfate.
AbstractList	Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure‐to‐biological function axis. In this review we focus on chemical approaches to and methodology improvements for the synthesis of these essential sugars (from 2015 onwards). We first consider advances in accessing the heparin‐derived pentasaccharide anticoagulant fondaparinux. This is followed by heparan sulfate targets, including key building block synthesis, oligosaccharide construction and chemical sulfation techniques. We end with a consideration of technological improvements to traditional, solution‐phase synthesis approaches that are increasingly being utilised. This review describes recent advances (2015 onwards) surrounding the chemical synthesis of heparin and heparan sulfate. Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure‐to‐biological function axis. In this review we focus on chemical approaches to and methodology improvements for the synthesis of these essential sugars (from 2015 onwards). We first consider advances in accessing the heparin‐derived pentasaccharide anticoagulant fondaparinux. This is followed by heparan sulfate targets, including key building block synthesis, oligosaccharide construction and chemical sulfation techniques. We end with a consideration of technological improvements to traditional, solution‐phase synthesis approaches that are increasingly being utilised. Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure-to-biological function axis. In this review we focus on chemical approaches to and methodology improvements for the synthesis of these essential sugars (from 2015 onwards). We first consider advances in accessing the heparin-derived pentasaccharide anticoagulant fondaparinux. This is followed by heparan sulfate targets, including key building block synthesis, oligosaccharide construction and chemical sulfation techniques. We end with a consideration of technological improvements to traditional, solution-phase synthesis approaches that are increasingly being utilised.Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological importance. As such, their efficiency of synthesis represents a key requirement, to further understand and exploit the H/HS structure-to-biological function axis. In this review we focus on chemical approaches to and methodology improvements for the synthesis of these essential sugars (from 2015 onwards). We first consider advances in accessing the heparin-derived pentasaccharide anticoagulant fondaparinux. This is followed by heparan sulfate targets, including key building block synthesis, oligosaccharide construction and chemical sulfation techniques. We end with a consideration of technological improvements to traditional, solution-phase synthesis approaches that are increasingly being utilised.
Author	Pongener, Imlirenla O'Shea, Conor Watkinson, Michael Wootton, Hannah Miller, Gavin J.
Author_xml	– sequence: 1 givenname: Imlirenla surname: Pongener fullname: Pongener, Imlirenla organization: Keele University – sequence: 2 givenname: Conor surname: O'Shea fullname: O'Shea, Conor organization: Keele University – sequence: 3 givenname: Hannah surname: Wootton fullname: Wootton, Hannah organization: Keele University – sequence: 4 givenname: Michael surname: Watkinson fullname: Watkinson, Michael organization: Keele University – sequence: 5 givenname: Gavin J. surname: Miller fullname: Miller, Gavin J. email: g.j.miller@keele.ac.uk organization: Keele University
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/34523797$$D View this record in MEDLINE/PubMed
BookMark	eNp90UtLxDAQB_Agiuvr6FUKXrx0zaNtmqOs6wMEwdVziOmEzdKma9Iq--2NdldhQU_5B34zDDOHaNe1DhA6JXhMMKaXnfZjimnMhLMddEByWqa4EGT3O_O0FEKM0GEIi0hIxvk-GrEsp4wLfoCm1_AOdbtswHUhsS7p5pBM5tBYrepktnLxH2xIWpPcwVL5KJSrhqxcMutrozo4RntG1QFO1u8RermZPk_u0ofH2_vJ1UOqM56xVCvIS1HhkmqjK8YxxlBWWrxmihmqqwJUpQth4nQmE8AKnTOhSF5hU5S4NOwIXQx9l7596yF0srFBQ10rB20fJM05FZRlPI_0fIsu2t67OJ2kBSaiKDjJojpbq_61gUouvW2UX8nNgiJgA9C-DcGDkdp2qrOt67yytSRYfp1BxjPInzPEqnSratP4L88H_2FrWP2P5fPk6bfyE57Yl8I
CitedBy_id	crossref_primary_10_1016_j_carbpol_2024_122220 crossref_primary_10_1039_D2QO00439A crossref_primary_10_1002_ange_202422766 crossref_primary_10_1002_cjoc_70116 crossref_primary_10_1016_j_ijbiomac_2023_125821 crossref_primary_10_1002_anie_202422766 crossref_primary_10_1016_j_cbpa_2024_102455 crossref_primary_10_1002_ejoc_202400587 crossref_primary_10_1016_j_carbpol_2024_122216 crossref_primary_10_1002_adma_202400436 crossref_primary_10_1016_j_enzmictec_2023_110324 crossref_primary_10_1016_j_carres_2022_108579 crossref_primary_10_1002_ange_202211985 crossref_primary_10_3390_M1847 crossref_primary_10_1016_j_carres_2023_108759 crossref_primary_10_1021_acs_biomac_5c00576 crossref_primary_10_1016_j_ijbiomac_2022_12_090 crossref_primary_10_1039_D5OB00746A crossref_primary_10_1002_anie_202211985
Cites_doi	10.1021/jacs.9b03266 10.1002/anie.201908805 10.1039/C4RA17050D 10.1016/j.carres.2014.06.026 10.1016/j.bmcl.2017.04.013 10.1021/acs.joc.9b01594 10.1021/acs.joc.0c01881 10.1002/anie.200300640 10.1002/anie.202007211 10.1039/C5QO00320B 10.1016/j.bmc.2012.11.053 10.1039/C8SC01743C 10.1039/D0CB00199F 10.1039/C9QO00480G 10.3390/molecules20046167 10.1093/glycob/2.6.523 10.1039/C4RA09854D 10.1021/jacs.6b08161 10.1002/ajoc.201500113 10.1039/c3sc51217g 10.1002/ange.200300640 10.1039/C5SC02091C 10.1039/C5CC05222J 10.1002/ange.202007211 10.1021/jo400467g 10.1021/jacs.0c00005 10.1021/acs.joc.6b00144 10.1016/j.carres.2016.10.005 10.1007/BFb0119251 10.1021/jo502776f 10.1083/jcb.116.5.1273 10.1016/j.carres.2016.10.008 10.1055/s-0040-1721319 10.1002/ange.201800387 10.1002/ange.201908805 10.1021/acs.joc.5b02172 10.1021/acs.joc.5b02468 10.1039/C9QO00581A 10.1039/D0OB00671H 10.1039/C5OB01706H 10.1039/C8OB02756K 10.1111/j.1742-4658.2012.08529.x 10.1021/jo300722y 10.1039/D0SC01140A 10.1021/ja071955l 10.1021/ja907358k 10.1002/chem.201204519 10.1021/jacs.7b01399 10.3389/fmicb.2016.00220 10.1021/acs.chemrev.6b00010 10.1002/ejoc.201900540 10.1016/j.cell.2020.09.033 10.1021/ol303112y 10.1002/anie.201800387 10.1038/nchembio.207 10.1021/acs.orglett.0c01386
ContentType	Journal Article
Copyright	2021 The Authors. Published by The Chemical Society of Japan & Wiley-VCH GmbH 2021 The Authors. Published by The Chemical Society of Japan & Wiley-VCH GmbH. 2021. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
Copyright_xml	– notice: 2021 The Authors. Published by The Chemical Society of Japan & Wiley-VCH GmbH – notice: 2021 The Authors. Published by The Chemical Society of Japan & Wiley-VCH GmbH. – notice: 2021. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
DBID	24P AAYXX CITATION CGR CUY CVF ECM EIF NPM 7QO 7T7 8FD C1K FR3 P64 7X8
DOI	10.1002/tcr.202100173
DatabaseName	Wiley Online Library Open Access CrossRef Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed Biotechnology Research Abstracts Industrial and Applied Microbiology Abstracts (Microbiology A) Technology Research Database Environmental Sciences and Pollution Management Engineering Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic
DatabaseTitle	CrossRef MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) Engineering Research Database Biotechnology Research Abstracts Technology Research Database Industrial and Applied Microbiology Abstracts (Microbiology A) Biotechnology and BioEngineering Abstracts Environmental Sciences and Pollution Management MEDLINE - Academic
DatabaseTitleList	CrossRef Engineering Research Database MEDLINE MEDLINE - Academic
Database_xml	– sequence: 1 dbid: 24P name: Wiley Online Library Open Access url: https://authorservices.wiley.com/open-science/open-access/browse-journals.html sourceTypes: Publisher – sequence: 2 dbid: NPM name: PubMed url: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 3 dbid: 7X8 name: MEDLINE - Academic url: https://search.proquest.com/medline sourceTypes: Aggregation Database
DeliveryMethod	fulltext_linktorsrc
Discipline	Chemistry
EISSN	1528-0691
EndPage	3255
ExternalDocumentID	34523797 10_1002_tcr_202100173 TCR202100173
Genre	article Journal Article Review
GrantInformation_xml	– fundername: UK Research and Innovation funderid: MR/T019522/1 – fundername: Engineering and Physical Sciences Research Council funderid: EP/T007397/1 – fundername: Keele University – fundername: Medical Research Council grantid: MR/T019522/1 – fundername: Engineering and Physical Sciences Research Council grantid: EP/T007397/1 – fundername: UK Research and Innovation grantid: MR/T019522/1
GroupedDBID	--- .3N .Y3 05W 0R~ 10A 123 1OC 24P 29B 31~ 33P 3WU 4.4 50Y 51W 51X 52M 52N 52O 52P 52S 52T 52W 52X 53G 5VS 66C 702 7PT 8-1 8UM AAESR AAHQN AAMMB AAMNL AANHP AANLZ AASGY AAXRX AAYCA AAZKR ABCQN ABCUV ABDBF ABEML ABIJN ABJNI ACAHQ ACBWZ ACCZN ACGFS ACIWK ACPOU ACPRK ACRPL ACSCC ACUHS ACXBN ACXQS ACYXJ ADBBV ADEOM ADKYN ADMGS ADNMO ADOZA ADXAS ADZMN AEFGJ AEIGN AENEX AEUYR AEYWJ AFBPY AFFPM AFGKR AFRAH AFWVQ AFZJQ AGHNM AGQPQ AGXDD AGYGG AHBTC AIDQK AIDYY AITYG AIURR ALMA_UNASSIGNED_HOLDINGS ALUQN ALVPJ AMYDB ASPBG AVWKF AZFZN AZVAB BDRZF BFHJK BMXJE BROTX BRXPI BY8 CS3 DCZOG DPXWK DR2 DRFUL DRSTM DU5 EBD EBS EJD F5P FEDTE G-S G.N GODZA HF~ HGLYW HVGLF HZ~ IX1 J0M LATKE LAW LC2 LC3 LEEKS LH- LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MSFUL MSSTM MXFUL MXSTM MY~ N9A O9- OIG P2W P4D Q11 QB0 QRW R.K ROL RX1 SUPJJ V2E W99 WBKPD WOHZO WQJ WXSBR WYUIH XG1 XV2 ZZTAW ~IA AAYXX CITATION CGR CUY CVF ECM EIF NPM 7QO 7T7 8FD C1K FR3 P64 7X8
ID	FETCH-LOGICAL-c4743-cae589d082cfcd37000e8dc9b4a3f2cd6eadc69f452f49e36c539a15d0f6808f3
IEDL.DBID	24P
ISICitedReferencesCount	28
ISICitedReferencesURI	http://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestLinkType=CitingArticles&DestApp=WOS_CPL&KeyUT=000695916100001&url=https%3A%2F%2Fcvtisr.summon.serialssolutions.com%2F%23%21%2Fsearch%3Fho%3Df%26include.ft.matches%3Dt%26l%3Dnull%26q%3D
ISSN	1527-8999 1528-0691
IngestDate	Thu Jul 10 22:08:23 EDT 2025 Fri Jul 25 10:28:41 EDT 2025 Mon Jul 21 06:03:11 EDT 2025 Tue Nov 18 22:24:33 EST 2025 Sat Nov 29 02:10:19 EST 2025 Sun Jul 06 04:44:58 EDT 2025
IsDoiOpenAccess	true
IsOpenAccess	true
IsPeerReviewed	true
IsScholarly	true
Issue	11
Keywords	carbohydrates heparin glycosylation heparan sulfate glycosaminoglycan
Language	English
License	Attribution 2021 The Authors. Published by The Chemical Society of Japan & Wiley-VCH GmbH.
LinkModel	DirectLink
MergedId	FETCHMERGED-LOGICAL-c4743-cae589d082cfcd37000e8dc9b4a3f2cd6eadc69f452f49e36c539a15d0f6808f3
Notes	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23
OpenAccessLink	https://onlinelibrary.wiley.com/doi/abs/10.1002%2Ftcr.202100173
PMID	34523797
PQID	2601966714
PQPubID	1006501
PageCount	18
ParticipantIDs	proquest_miscellaneous_2572923475 proquest_journals_2601966714 pubmed_primary_34523797 crossref_citationtrail_10_1002_tcr_202100173 crossref_primary_10_1002_tcr_202100173 wiley_primary_10_1002_tcr_202100173_TCR202100173
PublicationCentury	2000
PublicationDate	November 2021
PublicationDateYYYYMMDD	2021-11-01
PublicationDate_xml	– month: 11 year: 2021 text: November 2021
PublicationDecade	2020
PublicationPlace	United States
PublicationPlace_xml	– name: United States – name: Hoboken
PublicationTitle	Chemical record
PublicationTitleAlternate	Chem Rec
PublicationYear	2021
Publisher	Wiley Subscription Services, Inc
Publisher_xml	– name: Wiley Subscription Services, Inc
References	2015; 13 2019; 2019 2007; 129 2004 2004; 43 116 2015; 6 2015; 5 2013; 4 2019; 6 2015; 4 2021; 2 2013; 21 2020; 85 2020; 120 2015; 51 2020; 142 2017; 27 2020; 183 1998 2020 2020; 59 132 2019; 17 2015; 80 2020; 11 2009; 131 2019; 141 2012; 77 2019 2019; 58 131 2017; 139 2020; 18 2013; 19 2018; 9 2016; 7 2013; 15 2019; 84 2016; 3 2013; 78 2015; 20 2018 2018; 57 130 1992; 116 2016; 116 2016; 138 2016; 435 2009; 5 2016; 81 2020; 22 2012; 279 1992; 2 2014; 400 e_1_2_7_5_1 e_1_2_7_3_1 e_1_2_7_9_1 e_1_2_7_7_1 e_1_2_7_19_1 e_1_2_7_17_1 e_1_2_7_15_1 e_1_2_7_41_1 e_1_2_7_1_1 e_1_2_7_13_1 e_1_2_7_43_1 e_1_2_7_11_1 e_1_2_7_45_1 e_1_2_7_47_1 e_1_2_7_26_1 e_1_2_7_49_1 e_1_2_7_28_1 Driguez H. (e_1_2_7_32_1) 1998 e_1_2_7_50_1 e_1_2_7_25_1 e_1_2_7_31_1 e_1_2_7_52_1 e_1_2_7_23_2 e_1_2_7_31_2 e_1_2_7_23_1 e_1_2_7_33_1 e_1_2_7_54_1 e_1_2_7_21_1 e_1_2_7_35_1 e_1_2_7_37_1 e_1_2_7_39_1 e_1_2_7_6_1 e_1_2_7_4_1 e_1_2_7_8_1 e_1_2_7_18_1 e_1_2_7_16_1 e_1_2_7_40_1 e_1_2_7_2_1 e_1_2_7_14_1 e_1_2_7_42_1 e_1_2_7_12_1 e_1_2_7_44_1 e_1_2_7_10_1 e_1_2_7_46_1 e_1_2_7_48_1 e_1_2_7_27_1 e_1_2_7_48_2 e_1_2_7_29_1 Hansen S. U. (e_1_2_7_38_1) 2013; 4 e_1_2_7_51_1 e_1_2_7_30_1 e_1_2_7_53_1 e_1_2_7_24_1 e_1_2_7_22_1 e_1_2_7_34_1 e_1_2_7_34_2 e_1_2_7_20_1 e_1_2_7_36_1
References_xml	– volume: 183 start-page: 1 year: 2020 end-page: 15 publication-title: Cell – volume: 120 start-page: 1700 year: 2020 end-page: 1715 publication-title: Thromb. Haemostasis – volume: 400 start-page: 44 year: 2014 end-page: 53 publication-title: Carbohydr. Res. – volume: 5 start-page: 743 year: 2009 end-page: 748 publication-title: Nat. Chem. Biol. – volume: 5 start-page: 19027 year: 2015 end-page: 19033 publication-title: RSC Adv. – volume: 142 start-page: 5282 year: 2020 end-page: 5292 publication-title: J. Am. Chem. Soc. – volume: 15 start-page: 88 year: 2013 end-page: 91 publication-title: Org. Lett. – volume: 20 start-page: 6167 year: 2015 end-page: 6180 publication-title: Molecules – volume: 59 132 start-page: 18435 18593 year: 2020 2020 end-page: 18441 18599 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 116 start-page: 8193 year: 2016 end-page: 8255 publication-title: Chem. Rev. – volume: 5 start-page: 9325 year: 2015 end-page: 9327 publication-title: RSC Adv. – volume: 27 start-page: 2424 year: 2017 end-page: 2427 publication-title: Bioorg. Med. Chem. Lett. – volume: 57 130 start-page: 5340 5438 year: 2018 2018 end-page: 5344 5442 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 80 start-page: 12265 year: 2015 end-page: 12279 publication-title: J. Org. Chem. – volume: 43 116 start-page: 3118 3180 year: 2004 2004 end-page: 3133 3196 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 3 start-page: 103 year: 2016 end-page: 109 publication-title: Org. Chem. Front. – volume: 81 start-page: 162 year: 2016 end-page: 184 publication-title: J. Org. Chem. – volume: 2 start-page: 523 year: 1992 end-page: 528 publication-title: Glycobiology – volume: 7 start-page: 220 year: 2016 publication-title: Front. Microbiol. – volume: 116 start-page: 1273 year: 1992 end-page: 1281 publication-title: J. Cell Biol. – volume: 2019 start-page: 2950 year: 2019 end-page: 2953 publication-title: Eur. J. Org. Chem. – volume: 19 start-page: 6817 year: 2013 end-page: 6823 publication-title: Chem. Eur. J. – volume: 9 start-page: 6685 year: 2018 end-page: 6691 publication-title: Chem. Sci. – volume: 81 start-page: 4464 year: 2016 end-page: 4474 publication-title: J. Org. Chem. – volume: 77 start-page: 7823 year: 2012 end-page: 7843 publication-title: J. Org. Chem. – volume: 2 start-page: 702 year: 2021 end-page: 712 publication-title: RSC Chem. Biol. – volume: 131 start-page: 17394 year: 2009 end-page: 17405 publication-title: J. Am. Chem. Soc. – volume: 279 start-page: 1177 year: 2012 end-page: 1197 publication-title: FEBS J. – volume: 435 start-page: 180 year: 2016 end-page: 194 publication-title: Carbohydr. Res. – volume: 13 start-page: 11208 year: 2015 end-page: 11219 publication-title: Org. Biomol. Chem. – volume: 435 start-page: 195 year: 2016 end-page: 207 publication-title: Carbohydr. Res. – volume: 141 start-page: 10309 year: 2019 end-page: 10314 publication-title: J. Am. Chem. Soc. – volume: 6 start-page: 6158 year: 2015 end-page: 6164 publication-title: Chem. Sci. – start-page: 85 year: 1998 end-page: 116 – volume: 6 start-page: 3116 year: 2019 end-page: 3120 publication-title: Org. Chem. Front. – volume: 6 start-page: 2718 year: 2019 end-page: 2725 publication-title: Org. Chem. Front. – volume: 139 start-page: 9534 year: 2017 end-page: 9543 publication-title: J. Am. Chem. Soc. – volume: 58 131 start-page: 18577 18750 year: 2019 2019 end-page: 18583 18756 publication-title: Angew. Chem. Int. Ed. Angew. Chem. – volume: 4 start-page: 1 year: 2013 end-page: 9 publication-title: Nat. Commun. – volume: 21 start-page: 4786 year: 2013 end-page: 4792 publication-title: Bioorg. Med. Chem. – volume: 17 start-page: 1817 year: 2019 end-page: 1821 publication-title: Org. Biomol. Chem. – volume: 138 start-page: 13059 year: 2016 end-page: 13067 publication-title: J. Am. Chem. Soc. – volume: 84 start-page: 15063 year: 2019 end-page: 15078 publication-title: J. Org. Chem. – volume: 18 start-page: 4728 year: 2020 end-page: 4733 publication-title: Org. Biomol. Chem. – volume: 51 start-page: 13846 year: 2015 end-page: 13849 publication-title: Chem. Commun. – volume: 4 start-page: 3218 year: 2013 end-page: 3222 publication-title: Chem. Sci. – volume: 4 start-page: 756 year: 2015 end-page: 762 publication-title: Asian J. Org. Chem. – volume: 11 start-page: 6393 year: 2020 end-page: 6404 publication-title: Chem. Sci. – volume: 22 start-page: 4638 year: 2020 end-page: 4642 publication-title: Org. Lett. – volume: 78 start-page: 6911 year: 2013 end-page: 6934 publication-title: J. Org. Chem. – volume: 129 start-page: 9222 year: 2007 end-page: 9235 publication-title: J. Am. Chem. Soc. – volume: 80 start-page: 3777 year: 2015 end-page: 3789 publication-title: J. Org. Chem. – volume: 85 start-page: 16082 year: 2020 end-page: 16098 publication-title: J. Org. Chem. – ident: e_1_2_7_20_1 doi: 10.1021/jacs.9b03266 – ident: e_1_2_7_23_1 doi: 10.1002/anie.201908805 – ident: e_1_2_7_22_1 doi: 10.1039/C4RA17050D – ident: e_1_2_7_30_1 doi: 10.1016/j.carres.2014.06.026 – ident: e_1_2_7_14_1 doi: 10.1016/j.bmcl.2017.04.013 – ident: e_1_2_7_35_1 doi: 10.1021/acs.joc.9b01594 – ident: e_1_2_7_44_1 doi: 10.1021/acs.joc.0c01881 – ident: e_1_2_7_34_1 doi: 10.1002/anie.200300640 – ident: e_1_2_7_48_1 doi: 10.1002/anie.202007211 – ident: e_1_2_7_47_1 doi: 10.1039/C5QO00320B – ident: e_1_2_7_9_1 doi: 10.1016/j.bmc.2012.11.053 – ident: e_1_2_7_15_1 doi: 10.1039/C8SC01743C – ident: e_1_2_7_10_1 doi: 10.1039/D0CB00199F – ident: e_1_2_7_18_1 doi: 10.1039/C9QO00480G – ident: e_1_2_7_26_1 doi: 10.3390/molecules20046167 – ident: e_1_2_7_1_1 doi: 10.1093/glycob/2.6.523 – ident: e_1_2_7_49_1 doi: 10.1039/C4RA09854D – volume: 4 start-page: 1 year: 2013 ident: e_1_2_7_38_1 publication-title: Nat. Commun. – ident: e_1_2_7_42_1 doi: 10.1021/jacs.6b08161 – ident: e_1_2_7_24_1 doi: 10.1002/ajoc.201500113 – ident: e_1_2_7_29_1 doi: 10.1039/c3sc51217g – ident: e_1_2_7_34_2 doi: 10.1002/ange.200300640 – ident: e_1_2_7_37_1 doi: 10.1039/C5SC02091C – ident: e_1_2_7_40_1 doi: 10.1039/C5CC05222J – ident: e_1_2_7_48_2 doi: 10.1002/ange.202007211 – ident: e_1_2_7_50_1 doi: 10.1021/jo400467g – ident: e_1_2_7_43_1 doi: 10.1021/jacs.0c00005 – ident: e_1_2_7_17_1 doi: 10.1021/acs.joc.6b00144 – ident: e_1_2_7_53_1 doi: 10.1016/j.carres.2016.10.005 – start-page: 85 volume-title: Glycosci. Synth. Substrate Analog. Mimetics year: 1998 ident: e_1_2_7_32_1 doi: 10.1007/BFb0119251 – ident: e_1_2_7_36_1 doi: 10.1021/jo502776f – ident: e_1_2_7_7_1 doi: 10.1083/jcb.116.5.1273 – ident: e_1_2_7_46_1 doi: 10.1016/j.carres.2016.10.008 – ident: e_1_2_7_5_1 doi: 10.1055/s-0040-1721319 – ident: e_1_2_7_31_2 doi: 10.1002/ange.201800387 – ident: e_1_2_7_23_2 doi: 10.1002/ange.201908805 – ident: e_1_2_7_25_1 doi: 10.1021/acs.joc.5b02172 – ident: e_1_2_7_13_1 doi: 10.1021/acs.joc.5b02468 – ident: e_1_2_7_33_1 doi: 10.1039/C9QO00581A – ident: e_1_2_7_52_1 doi: 10.1039/D0OB00671H – ident: e_1_2_7_39_1 doi: 10.1039/C5OB01706H – ident: e_1_2_7_51_1 doi: 10.1039/C8OB02756K – ident: e_1_2_7_2_1 doi: 10.1111/j.1742-4658.2012.08529.x – ident: e_1_2_7_28_1 doi: 10.1021/jo300722y – ident: e_1_2_7_54_1 doi: 10.1039/D0SC01140A – ident: e_1_2_7_16_1 doi: 10.1021/ja071955l – ident: e_1_2_7_45_1 doi: 10.1021/ja907358k – ident: e_1_2_7_3_1 doi: 10.1002/chem.201204519 – ident: e_1_2_7_41_1 doi: 10.1021/jacs.7b01399 – ident: e_1_2_7_8_1 doi: 10.3389/fmicb.2016.00220 – ident: e_1_2_7_11_1 doi: 10.1021/acs.chemrev.6b00010 – ident: e_1_2_7_21_1 doi: 10.1002/ejoc.201900540 – ident: e_1_2_7_4_1 doi: 10.1016/j.cell.2020.09.033 – ident: e_1_2_7_27_1 doi: 10.1021/ol303112y – ident: e_1_2_7_31_1 doi: 10.1002/anie.201800387 – ident: e_1_2_7_12_1 – ident: e_1_2_7_6_1 doi: 10.1038/nchembio.207 – ident: e_1_2_7_19_1 doi: 10.1021/acs.orglett.0c01386
SSID	ssj0011477
Score	2.4345715
SecondaryResourceType	review_article
Snippet	Heparin and heparan sulfate represent key members of the glycosaminoglycan family of carbohydrates and underpin considerable repertoires of biological...
SourceID	proquest pubmed crossref wiley
SourceType	Aggregation Database Index Database Enrichment Source Publisher
StartPage	3238
SubjectTerms	Carbohydrates Chemical Phenomena Chemical synthesis Construction glycosaminoglycan Glycosaminoglycans glycosylation Heparan sulfate Heparin Heparitin Sulfate Oligosaccharides Structure-function relationships Sugar Sulfates Sulfation
Title	Developments in the Chemical Synthesis of Heparin and Heparan Sulfate
URI	https://onlinelibrary.wiley.com/doi/abs/10.1002%2Ftcr.202100173 https://www.ncbi.nlm.nih.gov/pubmed/34523797 https://www.proquest.com/docview/2601966714 https://www.proquest.com/docview/2572923475
Volume	21
WOSCitedRecordID	wos000695916100001&url=https%3A%2F%2Fcvtisr.summon.serialssolutions.com%2F%23%21%2Fsearch%3Fho%3Df%26include.ft.matches%3Dt%26l%3Dnull%26q%3D
hasFullText	1
inHoldings	1
isFullTextHit
isPrint
journalDatabaseRights	– providerCode: PRVWIB databaseName: Wiley Online Library Full Collection 2020 customDbUrl: eissn: 1528-0691 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0011477 issn: 1527-8999 databaseCode: DRFUL dateStart: 20010101 isFulltext: true titleUrlDefault: https://onlinelibrary.wiley.com providerName: Wiley-Blackwell
link	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1JS8QwFH64gV7cl7oRQTxZbJukaY4yzjAHEXGBuZVOFhiQjFhH8N_70naqgyiIl5LQpElftu81zfcBnEbSUqO4qgRN0EHhOhway0ObCC2ZpSpjtdiEuLnJBgN52-ic-rMwNT9E-8HNj4xqvvYDvBiWF5-koThRoXuXeA4hQedhMY5p5rUbEnbbbiPErJJe9NKtIToWsiHZxAdczGSfXZS-Ic1Z4FqtPL21f9d5HVYb0Eku616yAXPGbcJyZ6r1tgXdL_8OlWTkCMJCMuUSIPfvDuPlqCRjS_rG6xY6UjhdhwtH7idPFjHrNjz2ug-dftgILISKeWpSVRieSY0oQFmlqcDp0WRaySErqE2UTrGbqVRaxhPLpKGp4lQWMdeR9Yodlu7Aghs7swdEUG1SlhpEZIqZKCp0xAyLVIZwiWc6CuB8auFcNezjXgTjKa95k5McbZO3tgngrE3-XNNu_JTwcNpceTP6ytzTpKEbJ2IWwEl7G03qN0MKZ8YTTMPRrUgoEzyA3bqZ25IovjAVUgQQVa35exXyh85dG9n_e5YDWPHh-oDjISy8vkzMESypt9dR-XJcdWi8ikF2DItXd73H6w8MnPU9
linkProvider	Wiley-Blackwell
linkToHtml	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1bS8MwFD54A33xfqnXCOKTZV2TNM2jDGWiDtEJvpWaCwwkE-sE_70nbVcdoiC-NW3apicnyXeS5vsAjiJpqVFclYImGKBwHT4ay0MbCy2ZpSplldiE6PXShwd582UXf8UP0Uy4-ZZR9te-gfsJ6dYnayj2VBjfxZ5ESNBpmGU40nhPj9lNs47QZqX2otduDTGykDXLJj6gNXH75Kj0DWpOItdy6Dlf-n-hl2Gxhp3ktPKTFZgybhXmO2O1tzU4-_L3UEEGjiAwJGM2AXL37jBdDAoytKRrvHKhI7nT1XHuyN3oySJqXYf787N-pxvWEguhYp6cVOWGp1IjDlBWaSqwgzSpVvKR5dTGSifoaCqRlvHYMmloojiVeZvryHrNDks3YMYNndkCIqg2CUsMYjLFTBTlOmKGRSpFwMRTHQVwMjZxpmr-cS-D8ZRVzMlxhrbJGtsEcNxkf66IN37KuDuur6xuf0XmidIwkBNtFsBhcxlN6pdDcmeGI8zDMbCIKRM8gM2qnps3UfxgKqQIICqr8_ciZP3ObZPY_vstBzDf7V9fZVcXvcsdWPDnq-2OuzDz-jIyezCn3l4Hxct-6d0fRv_2oA
linkToPdf	http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1JS8QwFH7oKOrFfalrBPFksdMkTXOU0UFRBnEBb6VmgQHJiHUE_70vbac6iIJ4a9rXNH3Zvtc03wdwEElLjeKqFDTBAIXr8NFYHtpYaMksVSmrxCZEr5c-PMjrL7v4K36I5oOb7xnleO07uHnW9viTNRRHKozvYk8iJOgkTDEvJNOCqdOb7v1Vs5LQZqX6oldvDTG2kDXPJmZxPJbB-Lz0DWyOY9dy8uku_L_YizBfA09yUrWUJZgwbhlmOyO9txU4-_L_UEH6jiA0JCM-AXL77jBd9AsysOTceO1CR3Knq-Pckdvhk0Xcugr33bO7znlYiyyEinl6UpUbnkqNSEBZpanAIdKkWslHllMbK51gU1OJtIzHlklDE8WpzNtcR9ardli6Bi03cGYDiKDaJCwxiMoUM1GU64gZFqkUIRNPdRTA0cjFmaoZyL0QxlNWcSfHGfoma3wTwGFj_lxRb_xkuD2qr6zugUXmqdIwlBNtFsB-cxld6hdEcmcGQ7ThGFrElAkewHpVz82TKL4wFVIEEJXV-XsRsrvOTZPY_PstezBzfdrNri56l1sw509X-x23ofX6MjQ7MK3eXvvFy27dvD8Abvz3tg
openUrl	ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Developments+in+the+Chemical+Synthesis+of+Heparin+and+Heparan+Sulfate&rft.jtitle=Chemical+record&rft.au=Pongener%2C+Imlirenla&rft.au=O%27Shea%2C+Conor&rft.au=Wootton%2C+Hannah&rft.au=Watkinson%2C+Michael&rft.date=2021-11-01&rft.issn=1527-8999&rft.eissn=1528-0691&rft.volume=21&rft.issue=11&rft.spage=3238&rft.epage=3255&rft_id=info:doi/10.1002%2Ftcr.202100173&rft.externalDBID=10.1002%252Ftcr.202100173&rft.externalDocID=TCR202100173
thumbnail_l	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1527-8999&client=summon
thumbnail_m	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1527-8999&client=summon
thumbnail_s	http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1527-8999&client=summon