α-Methyl and β,β-dimethyl amino acids

Published on 09/02/2017

α-Methyl and alkyl-amino acids can be produced by a number of platforms, where the (2S,4S)-4-methyl-2-phenyloxazolidin-5-one scaffold is one of the most popular one.

α-Methyl and alkyl-amino acids can be produced by a number of platforms, where the (2S,4S)-4-methyl-2-phenyloxazolidin-5-one scaffold is one of the most popular one. We optimize published procedures and have own proprietary ones, which enable us to supply all kinds of protected α-methyl amino acids.

Such building blocks are being used to build up resistance towards proteolytic digestion of corresponding peptides or to implement certain amid bind conformation.

An alternative are β,β-dimethylated amino acids, where structure of the α-carbon is being maintained and the stability providing property comes through derivatization at the neighbouring carbon.

With tert-leucine and penicillamine there are already derivatives known in the peptide community, however, access to other analogues is very unique and available only through our specific synthesis platform.

References:

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A General Method for Making Peptide Therapeutics Resistant to Serine Protease Degradation: Application to Dipeptidyl Peptidase IV Substrates; K.R. Heard, W. Wu, Y. Li, P. Zhao, I. Woznica, J.H. Lai, M. Beinborn, D.G. Sanford, M.T. Dimare, A.K. Chiluwal, D.E. Peters, D. Whicher, J.L. Sudmeier, W.W. Bachovchin; J. Med. Chem. 2013; 56: 8339−8351; dx.doi.org/10.1021/jm400423p.