Total chemical synthesis of human thyroid-stimulating hormone (hTSH) β-subunit: Application of arginine-tagged acetamidomethyl (AcmR) protecting groups

被引：9
作者：
Brailsford, John A. [1 ]
Stockdill, Jennifer L. [1 ]
Axelrod, Abram J. [1 ]
Peterson, Michael T. [1 ]
Vadola, Paul A. [1 ]
Johnston, Eric, V [1 ]
Danishefsky, Samuel J. [1 ]
机构：
[1] Mem Sloan Kettering Canc Ctr, Lab Bioorgan Chem, 1275 York Ave, New York, NY 10065 USA
来源：
TETRAHEDRON | 2018年 / 74卷 / 15期
基金：
美国国家卫生研究院;
关键词：
Glycoprotein; Thyroid-stimulating hormone; Peptide chemistry; HUMAN THYROTROPIN; GLYCOPROTEIN HORMONES; METABOLIC-CLEARANCE; MEMBRANE-PROTEINS; ALPHA-SUBUNIT; PURIFICATION; PEPTIDES; LIGATION; STRATEGY;
D O I：
10.1016/j.tet.2018.02.067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The beta-subunit of human thyroid stimulating hormone (hTSH) has been synthesized as a single glycoform bearing a chitobiose disaccharide at the native glycosylation site. Key to the successful completion of this synthesis was the introduction of an arginine-tagged acetamidomethyl group, which served to greatly facilitate handling of a glycopeptide fragment with poor aqueous solubility. This general solution to the challenge of working with intractable peptides is expected to find wide use in protein synthesis. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1951 / 1956
页数：6
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