First total synthesis of cyanopterin, a pterin glycoside isolated from a cyanobacterium

IF 3.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-12-01 Epub Date: 2025-10-21 DOI:10.1016/j.carres.2025.109710

Tadashi Hanaya, Yuta Maeda, Kazumasa Ejiri

引用次数: 0

Abstract

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.

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首次合成了从一种蓝藻菌中分离出来的蝶呤苷

本文首次合成并鉴定了从藻胞菌中分离得到的一种蝶呤苷类化合物蓝翅素。通过三个关键衍生物：d-葡萄糖醛酸盐、d-半乳糖和6-羟甲基蝶呤的聚合偶联实现了合成。α-选择性糖基化可以有效地构建葡萄糖醛酸-半乳糖双糖，而随后与6-羟甲基蝶呤衍生物进行β-特异性糖基化可以得到所需的蝶呤-双糖糖苷。最后的去保护提供了自然形态的蓝翅虫素，从而确认了其精确的结构。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".