Programmable one cycle–one disaccharide unit modular synthesis of hyaluronan and chondroitin hybrid glycans

Li, Shuang; Wang, Shuaishuai; Qu, Jingyao; Han, Je-Chin; Yang, Lin; Li, Yang; Li, Lei; Jia, Qidong; Chen, Congcong; Ling, Peixue; Fang, Junqiang

doi:10.1039/d2gc04071a

Cited by 3 publications

(1 citation statement)

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“…Enzymatic synthesis represents a promising approach for generating structurally defined glycoconjugates. 9 These strategies were employed to construct systematic glycan libraries of various functional glycans, such as chondroitin sulfate, 10 hyaluronan and chondroitin hybrid glycans, 11 and fucosylated glycans. 12 However, no enzymatic method has yet been reported for the fucosylation of chondroitin or its analogues.…”

Section: ■ Introductionmentioning

confidence: 99%

Programmable Enzymatic Toolbox for the Assembly of Fucosylated Chondroitin Derivatives

Yang,

Wang,

Chen

et al. 2023

ACS Catal.

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Fucosylated chondroitin sulfate (FuCS), a unique glycosaminoglycan derived from the body walls of sea cucumbers, plays a vital role in various physiological processes. Although the physiological importance of FuCS is well-documented, the biosynthesis pathway, especially α1−3 fucosylation, is still unclear, thus hindering the development of an enzymatic synthesis approach to access both it and its derivatives. Herein, we report a programmable enzymatic toolbox for the synthesis of fucosylated chondroitin derivatives. Two distinct microbial α1−3-fucosyltransferases were identified for the synthesis of fucosylated chondroitin. Through precise control over chondroitin backbone extension and fucosylation, 13 fucosylated chondroitin oligosaccharides were assembled. Additionally, the synthetic toolbox has been further adapted for the fucosylation of chondroitin sulfate A, setting the stage for the formulation of a FuCS glycan library. This work demonstrates a possible biosynthetic pathway of FuCS and paves the way for the synthesis of this intriguing biomolecule.

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