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Fmoc‐2‐mercaptobenzothiazole, for the introduction of the Fmoc moiety free of side‐reactions
Author(s) -
IsidroLlobet Albert,
JustBaringo Xavier,
Ewenson Ariel,
Álvarez Mercedes,
Albericio Fernando
Publication year - 2007
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20732
Subject(s) - chemistry , tripeptide , reagent , moiety , amino acid , preprint , combinatorial chemistry , side chain , organic chemistry , polymer , biochemistry , world wide web , computer science
A double side‐reaction, consisting in the formation of Fmoc‐β‐Ala‐OH and Fmoc‐β‐Ala‐AA‐OH, during the preparation of Fmoc protected amino acids (Fmoc‐AA‐OH) with Fmoc‐OSu is discussed. Furthermore, the new Fmoc‐2‐MBT reagent is proposed for avoiding these side‐reactions as well as the formation of the Fmoc‐dipeptides (Fmoc‐AA‐AA‐OH) and even tripeptides, which is another important side‐reaction when chloroformates such as Fmoc‐Cl is used for the protection of the α‐amino function of the amino acids. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 88: 733–737, 2007. This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com