One-pot full peptide deprotection in Fmoc-based solid-phase peptide synthesis: methionine sulfoxide reduction with Bu4NBr

Authors
Taboada, L Nicolas, E Giralt, E
Citation
L. Taboada et al., One-pot full peptide deprotection in Fmoc-based solid-phase peptide synthesis: methionine sulfoxide reduction with Bu4NBr, TETRAHEDR L, 42(10), 2001, pp. 1891-1893
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
10
Year of publication
2001
Pages
1891 - 1893
Database
ISI
SICI code
0040-4039(20010304)42:10<1891:OFPDIF>2.0.ZU;2-C
Abstract
The reduction of methionine sulfoxide with Bu4NBr in TFA is reported. The u se of this reagent in conjunction with Fmoc chemistry-based acidolytic cock tails and the short reaction times that are needed for sulfoxide reduction (5 min) are the main advantages of this method, which is compatible with pe ptides containing aromatic amino acids. Cysteine is also stable under these conditions although, if desired, simultaneous disulfide formation can be a chieved in the absence of thiols. (C) 2001 Elsevier Science Ltd. All rights reserved.