First total synthesis of cyanopterin, a pterin glycoside isolated from a cyanobacterium.
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| Názov: | First total synthesis of cyanopterin, a pterin glycoside isolated from a cyanobacterium. |
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| Autori: | Hanaya T; Department of Chemistry, Faculty of Science, Okayama University, Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan. Electronic address: hanaya@cc.okayama-u.ac.jp., Maeda Y; Department of Chemistry, Faculty of Science, Okayama University, Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan., Ejiri K; Department of Chemistry, Faculty of Science, Okayama University, Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan. |
| Zdroj: | Carbohydrate research [Carbohydr Res] 2025 Dec; Vol. 558, pp. 109710. Date of Electronic Publication: 2025 Oct 21. |
| Spôsob vydávania: | Journal Article |
| Jazyk: | English |
| Informácie o časopise: | Publisher: Elsevier Country of Publication: Netherlands NLM ID: 0043535 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-426X (Electronic) Linking ISSN: 00086215 NLM ISO Abbreviation: Carbohydr Res Subsets: MEDLINE |
| Imprint Name(s): | Publication: Amsterdam : Elsevier Original Publication: Amsterdam. |
| Výrazy zo slovníka MeSH: | Pterins*/chemistry , Pterins*/chemical synthesis , Pterins*/isolation & purification , Glycosides*/chemistry , Glycosides*/chemical synthesis , Glycosides*/isolation & purification , Synechocystis*/chemistry , Cyanobacteria*/chemistry, Glycosylation |
| Abstrakt: | Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. The first total synthesis and structural identification of cyanopterin, a pterin glycoside isolated from the cyanobacterium Synechocystis sp. PCC 6803, has been accomplished. The synthesis was achieved by convergent coupling of three key derivatives: d-glucuronate, d-galactose, and 6-hydroxymethylpterin. An α-selective glycosylation enabled efficient construction of the glucuronate-galactose disaccharide, while subsequent β-exclusive glycosylation with the 6-hydroxymethylpterin derivative furnished the desired pterin-disaccharide glycoside. Final deprotection provided cyanopterin in its natural form, allowing confirmation of its precise structure. (Copyright © 2025 Elsevier Ltd. All rights reserved.) |
| Contributed Indexing: | Keywords: 6-Hydroxymethylpterin; Cyanopterin; Glycosylation; Pterin glycoside; Structural identification |
| Substance Nomenclature: | 0 (Pterins) 0 (Glycosides) |
| Entry Date(s): | Date Created: 20251025 Date Completed: 20251107 Latest Revision: 20251107 |
| Update Code: | 20251108 |
| DOI: | 10.1016/j.carres.2025.109710 |
| PMID: | 41138370 |
| Databáza: | MEDLINE |
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Nájsť tento článok vo Web of Science | Abstrakt: | Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.<br />The first total synthesis and structural identification of cyanopterin, a pterin glycoside isolated from the cyanobacterium Synechocystis sp. PCC 6803, has been accomplished. The synthesis was achieved by convergent coupling of three key derivatives: d-glucuronate, d-galactose, and 6-hydroxymethylpterin. An α-selective glycosylation enabled efficient construction of the glucuronate-galactose disaccharide, while subsequent β-exclusive glycosylation with the 6-hydroxymethylpterin derivative furnished the desired pterin-disaccharide glycoside. Final deprotection provided cyanopterin in its natural form, allowing confirmation of its precise structure.<br /> (Copyright © 2025 Elsevier Ltd. All rights reserved.) |
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| ISSN: | 1873-426X |
| DOI: | 10.1016/j.carres.2025.109710 |