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The chemical ligation of selectively S-acylated cysteine peptides to form native peptides via 5-, 11-and 14-membered cyclic transition states
Faculty
Pharmacy
Year:
2010
Type of Publication:
Article
Pages:
2316-2319
Authors:
Abo-Dya, Nader E, Katritzky, Alan R, Abdel-Samii, Zakaria K, Tala, Srinivasa R
DOI:
10.1039/c003234d
Journal:
ORGANIC \& BIOMOLECULAR CHEMISTRY ROYAL SOC CHEMISTRY
Volume:
8
Research Area:
Chemistry
ISSN
ISI:000277399300004
Keywords :
, chemical ligation , selectively S-acylated cysteine peptides
Abstract:
Cysteine and C-terminal cysteine peptides are selectively S-acylated at 0-20 degrees C by N-(Pg-alpha-aminoacyl)benzotriazoles to give N-Pg-S-acyl-isodi-, -isotri-, and -isotetra-peptides isolated in good yields. N-Fmoc-S-acyl-isopeptides are Fmoc deprotected to afford free S-acyl-isopeptides isolated in high yields. S-Acyl-isodi-, S-acyl-isotetra-, and S-acyl-isopenta-peptides undergo chemical ligation; migration of the cysteine S-acyl groups to the N-terminal amino acids via 5-, 11-, and 14-membered transition states giving the corresponding native di-, tetra-, and penta-peptides. By contrast, the S-acyl-isotripeptide prefers intermolecular acylation from one molecule to another over an 8-membered intramolecular transition state. The developed methodology allows convenient isolation of stable, unprotected S-acyl cysteine peptides including the first isolation of S-acyl-isopeptides, which should facilitate the investigation of ligation by physical organic chemistry techniques.
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