Current routes used to prepare alternating peptides, such as by Solid Phase Peptide Synthesis (SPPS), are prohibitively costly and inefficient since they require tedious step-by-step synthetic methodology. For the first time we report a general de-novo chemo-enzymatic route for preparing alternating peptides.  In the first step, dipeptide AG-OEt is chemically synthesized by coupling Boc-A-OSu with G-OEt. After N-boc removal, AG-OEt was oligomerized by protease-catalysis. Oligomerizations conducted at 40 oC at pH 7.5 catalyzed by papain gave perfectly alternating products with %-yield and DPavg of ~80% and 9.4�0.3, respectively, in 30 s. Acknowledgements  The authors are grateful for financial Support from the industrial members (BASF, Covidien, Firmenich, Novozymes, PepsiCo and Sherwin Williams) of our graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at NYU-POLY.

Simplifying oligopeptide synthesis by a unique chemo-enzymatic strategy

244th National Meeting (2012)

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