Fmoc-2-mercaptobenzothiazole, for the introduction of the Fmoc moiety free of side-reactions

✍ Scribed by Albert Isidro-Llobet; Xavier Just-Baringo; Ariel Ewenson; Mercedes Álvarez; Fernando Albericio

• Book ID: 101723169
• Publisher: Wiley (John Wiley & Sons)
• Year: 2007
• Tongue: English
• Weight: 381 KB
• Volume: 88
• Category: Article
• ISSN: 0006-3525
• DOI: 10.1002/bip.20732

✦ Synopsis

Abstract

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.

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