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

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Abstract

A double side-reaction, consisting in the formation of Fmoc-beta-Ala-OH and Fmoc-beta-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 alpha-amino function of the amino acids.

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