Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of S-Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis
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- 作者：Scott B. Cohen and Randall L. Halcomb
- 刊名：Journal of the American Chemical Society
- 出版年：2002
- 出版时间：March 20, 2002
- 年：2002
- 卷：124
- 期：11
- 页码：2534 - 2543
- 全文大小：143K
- 年卷期：v.124,no.11(March 20, 2002)
- ISSN：1520-5126
文摘
Cyclic sulfamidates were synthesized in 60% yield from L-serine and allo-L-threonine, respectively.These sulfamidates reacted with a variety of unprotected 1-thio sugars in aqueous bicarbonate buffer (pH8) to afford the corresponding S-linked serine- and threonine-glycosyl amino acids with good diastereoselectivity (
97%) after hydrolysis of the N-sulfates. The serine-derived sulfamidate was incorporated intoa simple dipeptide to generate a reactive dipeptide substrate that underwent chemoselective ligation witha 1-thio sugar to afford an S-linked glycopeptide. This sulfamidate was also incorporated into a peptide ona solid support in conjunction with solid-phase peptide synthesis. Chemoselective ligation of a 1-thio sugarwith the cyclic sulfamidate was achieved on the solid support, followed by removal of the N-sulfate. Finally,the peptide chain of the resulting support-bound S-linked glycopeptide was extended using standard peptidesynthesis procedures.
97%) after hydrolysis of the N-sulfates. The serine-derived sulfamidate was incorporated intoa simple dipeptide to generate a reactive dipeptide substrate that underwent chemoselective ligation witha 1-thio sugar to afford an S-linked glycopeptide. This sulfamidate was also incorporated into a peptide ona solid support in conjunction with solid-phase peptide synthesis. Chemoselective ligation of a 1-thio sugarwith the cyclic sulfamidate was achieved on the solid support, followed by removal of the N-sulfate. Finally,the peptide chain of the resulting support-bound S-linked glycopeptide was extended using standard peptidesynthesis procedures.