Synfacts 2022; 18(07): 0813
DOI: 10.1055/s-0041-1737670
Peptide Chemistry

A Novel Reagent for Coupling of Amino Acid Chlorides with Amino Acid Esters

Rezensent(en):
Hisashi Yamamoto
,
Isai Ramakrishna
Babu SJ. Tantry. V. V. S. * Bangalore University, India
1-(t-Butyldimethylsilyloxy) Benzotriazole (TBDMS-OBt): A New and Novel Reagent for the Synthesis of Peptides.

Lett. Peptide Sci.. 2002;
09: 35-41
DOI: 10.1023/A:1021307501833
 

Significance

The development of novel and efficient coupling reagents for peptide-bond formation is a continuous and highly demanding area in peptide chemistry. In 2002, Tantry and Babu reported that 1-{[tert-butyl(dimethyl)silyl]oxy}benzotriazole (TBDMS-OBt) is an efficient coupling reagent­ for the synthesis of dipeptides from amino acid chlorides and amino acid esters.


Comment

TBDMS-OBt is an efficient coupling reagent­ for the coupling of Fmoc-amino acid chlorides with amino acid esters to produce a series of dipeptides in good yields. This reaction is also successful with N-methyl amino acid esters. The coupling reation is racemization free and the TBDMS-OBt coupling reagent can be synthesized in one step.




Publikationsverlauf

Artikel online veröffentlicht:
15. Juni 2022

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