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Studies on the acylation of hydroxy-functionalized resins using Fmoc amino acids activated using diisopropylcarbodiimide/HOBt or as acid fluorides

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
49
Issue
20
Identifiers
DOI: 10.1016/s0040-4020(01)85732-x

Abstract

Abstract The data presented suggests that esterification of hydroxy-functionalized resins with Fmoc-protected amino acids proceeds best in low polarity solvents such as CH 2Cl 2 and THF and that pyridine, as co-solvent, is a suitable acylation catalyst. This has been demonstrated using DIC/HOBt activation, as well as Fmoc-protected amino acid fluorides which are excellent reagents for rapid, racemization-free acylation of hydroxy-functionalized resins used in solid phase peptide synthesis.

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