Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A

Chao Cai; Kemal Solakyildirim; Bo Yang; Julie M. Beaudet; Amanda Weyers; Robert J. Linhardt; Fuming Zhang

doi:10.1016/j.carbpol.2011.08.075

Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A

Chao Cai, Kemal Solakyildirim, Bo Yang, Julie M. Beaudet, Amanda Weyers, Robert J. Linhardt, Fuming Zhang

Research output: Contribution to journal › Article › peer-review

51 Scopus citations

Abstract

Chondroitin sulfate-E (chondroitin-4,6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4-sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, ¹H NMR, ¹³C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A.

Original language	English
Pages (from-to)	822-829
Number of pages	8
Journal	Carbohydrate Polymers
Volume	87
Issue number	1
DOIs	https://doi.org/10.1016/j.carbpol.2011.08.075
State	Published - 4 Jan 2012
Externally published	Yes

Keywords

Chemical semi-synthesis
Chondroitin sulfate-A
Chondroitin sulfate-E
LCMS
NMR
PAGE
Surface plasmon resonance

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10.1016/j.carbpol.2011.08.075

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@article{dc409bf75f0547aa9929af70ab6db235,

title = "Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A",

abstract = "Chondroitin sulfate-E (chondroitin-4,6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4-sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, 1H NMR, 13C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A.",

keywords = "Chemical semi-synthesis, Chondroitin sulfate-A, Chondroitin sulfate-E, LCMS, NMR, PAGE, Surface plasmon resonance",

author = "Chao Cai and Kemal Solakyildirim and Bo Yang and Beaudet, {Julie M.} and Amanda Weyers and Linhardt, {Robert J.} and Fuming Zhang",

note = "Funding Information: This work was supported by grants from the funded by the National Institutes of Health HL101721 , HL096972 , GM38060 and 2T32GM067545 . ",

year = "2012",

month = jan,

day = "4",

doi = "10.1016/j.carbpol.2011.08.075",

language = "English",

volume = "87",

pages = "822--829",

journal = "Carbohydrate Polymers",

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T1 - Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A

AU - Cai, Chao

AU - Solakyildirim, Kemal

AU - Yang, Bo

AU - Beaudet, Julie M.

AU - Weyers, Amanda

AU - Linhardt, Robert J.

AU - Zhang, Fuming

N1 - Funding Information: This work was supported by grants from the funded by the National Institutes of Health HL101721 , HL096972 , GM38060 and 2T32GM067545 .

PY - 2012/1/4

Y1 - 2012/1/4

N2 - Chondroitin sulfate-E (chondroitin-4,6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4-sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, 1H NMR, 13C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A.

AB - Chondroitin sulfate-E (chondroitin-4,6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4-sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, 1H NMR, 13C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A.

KW - Chemical semi-synthesis

KW - Chondroitin sulfate-A

KW - Chondroitin sulfate-E

KW - LCMS

KW - NMR

KW - PAGE

KW - Surface plasmon resonance

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U2 - 10.1016/j.carbpol.2011.08.075

DO - 10.1016/j.carbpol.2011.08.075

M3 - Article

AN - SCOPUS:80054753106

SN - 0144-8617

VL - 87

SP - 822

EP - 829

JO - Carbohydrate Polymers

JF - Carbohydrate Polymers

IS - 1

ER -

Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A

Abstract

Keywords

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