Solid-phase synthesis of C-terminally modified peptides
In this paper, a straightforward and generic protocol is presented to label the C‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles a...
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| Vydáno v: | Journal of peptide science Ročník 12; číslo 11; s. 686 - 692 |
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| Hlavní autoři: | , , , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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Chichester, UK
John Wiley & Sons, Ltd
01.11.2006
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| Témata: | |
| ISSN: | 1075-2617, 1099-1387 |
| On-line přístup: | Získat plný text |
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| Abstract | In this paper, a straightforward and generic protocol is presented to label the C‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl‐amine (desirable for ‘click’ chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde‐functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid‐phase peptide synthesis protocol. Since one procedure can be applied for any given amine‐functional moiety, a robust method for C‐terminal peptide labeling is obtained. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd. |
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| AbstractList | In this paper, a straightforward and generic protocol is presented to label the C-terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine-functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl-amine (desirable for 'click' chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde-functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid-phase peptide synthesis protocol. Since one procedure can be applied for any given amine-functional moiety, a robust method for C-terminal peptide labeling is obtained. In this paper, a straightforward and generic protocol is presented to label the C‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl‐amine (desirable for ‘click’ chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde‐functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid‐phase peptide synthesis protocol. Since one procedure can be applied for any given amine‐functional moiety, a robust method for C‐terminal peptide labeling is obtained. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd. In this paper, a straightforward and generic protocol is presented to label the C-terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine-functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl-amine (desirable for 'click' chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde-functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid-phase peptide synthesis protocol. Since one procedure can be applied for any given amine-functional moiety, a robust method for C-terminal peptide labeling is obtained.In this paper, a straightforward and generic protocol is presented to label the C-terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine-functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl-amine (desirable for 'click' chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde-functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid-phase peptide synthesis protocol. Since one procedure can be applied for any given amine-functional moiety, a robust method for C-terminal peptide labeling is obtained. In this paper, a straightforward and generic protocol is presented to label the C ‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl‐amine (desirable for ‘click’ chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde‐functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid‐phase peptide synthesis protocol. Since one procedure can be applied for any given amine‐functional moiety, a robust method for C ‐terminal peptide labeling is obtained. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd. |
| Author | Geel, Remon V. van Hest, Jan C. M. Ten Brink, Hefziba T. Damen, Mark Meijer, Joris T. Löwik, Dennis W. P. M. |
| Author_xml | – sequence: 1 givenname: Hefziba T. surname: Ten Brink fullname: Ten Brink, Hefziba T. organization: Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands – sequence: 2 givenname: Joris T. surname: Meijer fullname: Meijer, Joris T. organization: Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands – sequence: 3 givenname: Remon V. surname: Geel fullname: Geel, Remon V. organization: Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands – sequence: 4 givenname: Mark surname: Damen fullname: Damen, Mark organization: Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands – sequence: 5 givenname: Dennis W. P. M. surname: Löwik fullname: Löwik, Dennis W. P. M. email: D.Lowik@science.ru.nl organization: Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands – sequence: 6 givenname: Jan C. M. surname: van Hest fullname: van Hest, Jan C. M. organization: Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/16953495$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/la047578x 10.1002/adma.200401849 10.1016/S1359-6446(03)02933-7 10.1002/qsar.200320006 10.1021/cc034014n 10.1021/ja974116f 10.1002/psc.614 10.1021/ja004099l 10.1039/b412930j 10.1016/j.tetlet.2004.11.026 10.1016/S0040-4039(00)01255-7 10.1039/b413973a 10.1021/jo990629o 10.1016/S0040-4039(00)00950-3 10.1002/(SICI)1521-3765(19991001)5:10<2787::AID-CHEM2787>3.0.CO;2-2 10.1039/b303749e 10.1039/b212638a |
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| References | Beythien J, White PD. A solid phase linker strategy for the direct synthesis of EDANS-labelled peptide substrates. Tetrahedron Lett. 2005; 46: 101-104. Christensen C, Schiodt CB, Foged NT, Meldal M. Solid phase combinatorial library of 1,3-azole containing peptides for the discovery of matrix metallo proteinase inhibitors. QSAR Comb. Sci. 2003; 22: 754-766. Guillaumie F, Kappel JC, Kelly NM, Barany G, Jensen KJ. Solid-phase synthesis of C-terminal peptide aldehydes from amino acetals anchored to a backbone amide linker (BAL) handle. Tetrahedron Lett. 2000; 41: 6131-6135. Shannon SK, Peacock MJ, Kates SA, Barany G. Solid-phase synthesis of lidocaine and procainamide analogues using backbone amide linker (BAL) anchoring. J. Comb. Chem. 2003; 5: 860-868. Kappel JC, Barany G. Backbone amide linker (BAL) strategy for N-alpha-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of peptide aldehydes. J. Pept. Sci. 2005; 11: 525-535. Jensen KJ, Alsina J, Songster MF, Vagner J, Albericio F, Barany G. Backbone Amide Linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides. J. Am. Chem. Soc. 1998; 120: 5441-5452. McClain DL, Woods HL, Oakley MG. Design and characterization of a heterodimeric coiled coil that forms exclusively with an antiparallel relative helix orientation. J. Am. Chem. Soc. 2001; 123: 3151-3152. Kolb HC, Sharpless KB. The growing impact of click chemistry on drug discovery. Drug Discov. Today 2003; 8: 1128-1137. Alsina J, Yokum TS, Albericio F, Barany G. Backbone amide linker (BAL) strategy for N-alpha-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters. J. Org. Chem. 1999; 64: 8761-8769. Löwik DWPM, Meijer T, van Hest JCM. Tuning secondary structure and self-assembly of amphiphilic peptides. Biopolymers 2005; 80: 597. Vojkovsky T. Detection of secondary-amines on solid-phase. Pept. Res. 1995; 8: 236-237. Opsteen JA, van Hest JCM. Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers. Chem. Commun. 2005; 57-59. Alsina J, Yokum TS, Albericio F, Barany G. A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus. Tetrahedron Lett. 2000; 41: 7277-7280. Gao XY, Matsui H. Peptide-based nanotubes and their applications in bionanotechnology. Adv. Mater. 2005; 17: 2037-2050. Löwik DWPM, van Hest JCM. Peptide based amphiphiles. Chem. Soc. Rev. 2004; 33: 234-245. Reynhout IC, Löwik DWPM, van Hest JCM, Cornelissen JJLM, Nolte RJM. Solid phase synthesis of biohybrid block copolymers. Chem. Commun. 2005; 602-604. Alsina J, Jensen KJ, Albericio F, Barany G. Solid-phase synthesis with tris(alkoxy)benzyl backbone amide linkage (BAL). Chem.-Eur. J. 1999; 5: 2787-2795. Löwik DWPM, Garcia-Hartjes J, Meijer JT, van Hest JCM. Tuning secondary structure and self-assembly of amphiphilic peptides. Langmuir 2005; 21: 524-526. Löwik DWPM, Linhardt JG, Adams PJHM, van Hest JCM. Non-covalent stabilization of a beta-hairpin peptide into liposomes. Org. Biomol. Chem. 2003; 1: 1827-1829. 2004; 33 2001; 123 2003; 8 2000; 41 2005; 21 2003; 5 2006 2005 2005; 80 1999; 64 2003; 1 2005; 17 1999; 5 2005; 11 2003; 22 1998; 120 1995; 8 2005; 46 Vojkovsky T (e_1_2_1_19_2) 1995; 8 Löwik DWPM (e_1_2_1_6_2) 2005; 80 e_1_2_1_7_2 e_1_2_1_4_2 e_1_2_1_5_2 e_1_2_1_2_2 e_1_2_1_11_2 e_1_2_1_22_2 e_1_2_1_3_2 e_1_2_1_12_2 e_1_2_1_20_2 e_1_2_1_10_2 e_1_2_1_21_2 e_1_2_1_15_2 e_1_2_1_16_2 e_1_2_1_13_2 e_1_2_1_14_2 e_1_2_1_8_2 e_1_2_1_17_2 e_1_2_1_9_2 e_1_2_1_18_2 |
| References_xml | – reference: Vojkovsky T. Detection of secondary-amines on solid-phase. Pept. Res. 1995; 8: 236-237. – reference: Alsina J, Yokum TS, Albericio F, Barany G. A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus. Tetrahedron Lett. 2000; 41: 7277-7280. – reference: Gao XY, Matsui H. Peptide-based nanotubes and their applications in bionanotechnology. Adv. Mater. 2005; 17: 2037-2050. – reference: Reynhout IC, Löwik DWPM, van Hest JCM, Cornelissen JJLM, Nolte RJM. Solid phase synthesis of biohybrid block copolymers. Chem. Commun. 2005; 602-604. – reference: Kappel JC, Barany G. Backbone amide linker (BAL) strategy for N-alpha-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of peptide aldehydes. J. Pept. Sci. 2005; 11: 525-535. – reference: Alsina J, Jensen KJ, Albericio F, Barany G. Solid-phase synthesis with tris(alkoxy)benzyl backbone amide linkage (BAL). Chem.-Eur. J. 1999; 5: 2787-2795. – reference: Opsteen JA, van Hest JCM. Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers. Chem. Commun. 2005; 57-59. – reference: McClain DL, Woods HL, Oakley MG. Design and characterization of a heterodimeric coiled coil that forms exclusively with an antiparallel relative helix orientation. J. Am. Chem. Soc. 2001; 123: 3151-3152. – reference: Löwik DWPM, Linhardt JG, Adams PJHM, van Hest JCM. Non-covalent stabilization of a beta-hairpin peptide into liposomes. Org. Biomol. Chem. 2003; 1: 1827-1829. – reference: Christensen C, Schiodt CB, Foged NT, Meldal M. Solid phase combinatorial library of 1,3-azole containing peptides for the discovery of matrix metallo proteinase inhibitors. QSAR Comb. Sci. 2003; 22: 754-766. – reference: Jensen KJ, Alsina J, Songster MF, Vagner J, Albericio F, Barany G. Backbone Amide Linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides. J. Am. Chem. Soc. 1998; 120: 5441-5452. – reference: Shannon SK, Peacock MJ, Kates SA, Barany G. Solid-phase synthesis of lidocaine and procainamide analogues using backbone amide linker (BAL) anchoring. J. Comb. Chem. 2003; 5: 860-868. – reference: Beythien J, White PD. A solid phase linker strategy for the direct synthesis of EDANS-labelled peptide substrates. Tetrahedron Lett. 2005; 46: 101-104. – reference: Guillaumie F, Kappel JC, Kelly NM, Barany G, Jensen KJ. Solid-phase synthesis of C-terminal peptide aldehydes from amino acetals anchored to a backbone amide linker (BAL) handle. Tetrahedron Lett. 2000; 41: 6131-6135. – reference: Löwik DWPM, Meijer T, van Hest JCM. Tuning secondary structure and self-assembly of amphiphilic peptides. Biopolymers 2005; 80: 597. – reference: Löwik DWPM, van Hest JCM. Peptide based amphiphiles. Chem. Soc. Rev. 2004; 33: 234-245. – reference: Kolb HC, Sharpless KB. The growing impact of click chemistry on drug discovery. Drug Discov. Today 2003; 8: 1128-1137. – reference: Löwik DWPM, Garcia-Hartjes J, Meijer JT, van Hest JCM. Tuning secondary structure and self-assembly of amphiphilic peptides. Langmuir 2005; 21: 524-526. – reference: Alsina J, Yokum TS, Albericio F, Barany G. Backbone amide linker (BAL) strategy for N-alpha-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters. J. Org. Chem. 1999; 64: 8761-8769. – volume: 22 start-page: 754 year: 2003 end-page: 766 article-title: Solid phase combinatorial library of 1,3‐azole containing peptides for the discovery of matrix metallo proteinase inhibitors publication-title: QSAR Comb. Sci. – volume: 21 start-page: 524 year: 2005 end-page: 526 article-title: Tuning secondary structure and self‐assembly of amphiphilic peptides publication-title: Langmuir – volume: 8 start-page: 1128 year: 2003 end-page: 1137 article-title: The growing impact of click chemistry on drug discovery publication-title: Drug Discov. Today – volume: 11 start-page: 525 year: 2005 end-page: 535 article-title: Backbone amide linker (BAL) strategy for N‐alpha‐9‐fluorenylmethoxycarbonyl (Fmoc) solid‐phase synthesis of peptide aldehydes publication-title: J. Pept. Sci. – start-page: 57 year: 2005 end-page: 59 article-title: Modular synthesis of block copolymers via cycloaddition of terminal azide and alkyne functionalized polymers publication-title: Chem. Commun. – volume: 64 start-page: 8761 year: 1999 end-page: 8769 article-title: Backbone amide linker (BAL) strategy for N‐alpha‐9‐fluorenylmethoxycarbonyl (Fmoc) solid‐phase synthesis of unprotected peptide p‐nitroanilides and thioesters publication-title: J. Org. Chem. – volume: 5 start-page: 2787 year: 1999 end-page: 2795 article-title: Solid‐phase synthesis with tris(alkoxy)benzyl backbone amide linkage (BAL) publication-title: Chem.—Eur. J. – start-page: 602 year: 2005 end-page: 604 article-title: Solid phase synthesis of biohybrid block copolymers publication-title: Chem. 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| Snippet | In this paper, a straightforward and generic protocol is presented to label the C‐terminus of a peptide with any desired moiety that is functionalized with a... In this paper, a straightforward and generic protocol is presented to label the C ‐terminus of a peptide with any desired moiety that is functionalized with a... In this paper, a straightforward and generic protocol is presented to label the C-terminus of a peptide with any desired moiety that is functionalized with a... |
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| SubjectTerms | Aldehydes - chemistry Amines - chemistry Amino Acid Sequence Biochemistry - methods labeled peptides modified peptides Molecular Sequence Data Peptides - chemical synthesis Polystyrenes - chemistry reductive amination Resins, Synthetic - chemistry solid-phase synthesis |
| Title | Solid-phase synthesis of C-terminally modified peptides |
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