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同型丝氨酸作为天冬氨酸前体用于合成含有天冬氨酸和硫酸化聚糖链的蛋白聚糖糖肽。

Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain.

机构信息

Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.

Chemistry Department, Faculty of Science, Benha University , Benha, Qaliobiya 13518, Egypt.

出版信息

J Org Chem. 2016 Dec 2;81(23):12052-12059. doi: 10.1021/acs.joc.6b02441. Epub 2016 Nov 10.

DOI:10.1021/acs.joc.6b02441
PMID:27809505
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5215661/
Abstract

Among many hurdles in synthesizing proteoglycan glycopeptides, one challenge is the incorporation of aspartic acid in the peptide backbone and acid sensitive O-sulfated glycan chains. To overcome this, a new strategy was developed utilizing homoserine as an aspartic acid precursor. The conversion of homoserine to aspartic acid in the glycopeptide was successfully accomplished by late stage oxidation using (2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (TEMPO) and bis(acetoxy)iodobenzene (BAIB). This is the first time that a glycopeptide containing aspartic acid and an O-sulfated glycan was synthesized.

摘要

在合成蛋白聚糖糖肽的诸多障碍中，一个挑战是在肽主链中并入天冬氨酸和酸敏感的 O-硫酸化聚糖链。为了克服这一困难，开发了一种新的策略，利用高丝氨酸作为天冬氨酸前体。通过使用（2,2,6,6-四甲基-哌啶-1-基）氧自由基（TEMPO）和双（乙酰氧基）碘苯（BAIB）进行后期氧化，成功地将高丝氨酸转化为糖肽中天冬氨酸。这是第一次合成含有天冬氨酸和 O-硫酸化聚糖的糖肽。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/b33584bcbf35/nihms839857f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/28f5146f3f58/nihms839857f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/0e9dfb141d3a/nihms839857f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/707e271baaee/nihms839857f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/52edbd4bf872/nihms839857f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/b33584bcbf35/nihms839857f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/28f5146f3f58/nihms839857f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/0e9dfb141d3a/nihms839857f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/707e271baaee/nihms839857f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/52edbd4bf872/nihms839857f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8196/5215661/b33584bcbf35/nihms839857f5.jpg

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本文引用的文献

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Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains.携带两条硫酸乙酰肝素聚糖链的syndecan-3糖肽的化学合成。
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