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Synthesis of O ‐Acyl Isopeptides
Author(s) -
Sohma Youhei,
Kiso Yoshiaki
Publication year - 2013
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201200023
Subject(s) - peptide , acylation , chemistry , residue (chemistry) , combinatorial chemistry , peptide synthesis , stereochemistry , solubility , acyl carrier protein , biochemistry , escherichia coli , organic chemistry , catalysis , gene
O ‐Acyl isopeptides, in which the N ‐acyl linkage on the hydroxyamino acid residue (e.g., Ser and Thr) is replaced with an O ‐acyl linkage, generally possess superior water‐solubility to their corresponding native peptides, as well as other distinct physicochemical properties. In addition, O ‐acyl isopeptides can be rapidly converted into their corresponding native peptide under neutral aqueous conditions through an O ‐to‐ N acyl migration. By exploiting these characteristics, researchers have applied the O ‐acyl isopeptide method to various peptide‐synthesis fields, such as the synthesis of aggregative peptides and convergent peptide synthesis. This O ‐acyl‐isopeptide approach also serves as a means to control the biological function of the peptide in question. Herein, we report the synthesis of O ‐acyl isopeptides and some of their applications.