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Protease-catalyzed Oligomerization of Hydrophobic Amino Acid Ethyl Esters in Homogeneous Reaction Media Using L-Phenylalanine as a Model System

Protease-catalyzed Oligomerization of Hydrophobic Amino Acid Ethyl Esters in Homogeneous Reaction Media Using L-Phenylalanine as a Model System

Kodandaraman Viswanathan, Ruth Omorebokhae, Geng Li, Richard A Gross

Biomacromolecules. 2010 Aug 9;11(8):2152-60.

PMID: 20690722

Abstract:

Enzymatic synthesis of oligopeptides from l-phenylalanine ethyl ester hydrochloride (l-Phe-Et.HCl) and other l-form hydrophobic amino acid ester hydrochlorides in water miscible organic cosolvents was studied. Different proteases, water miscible cosolvents, and effect of different ratios of water miscible cosolvents for protease-catalyzed oligo-phenylalanine [oligo(l-Phe)] were compared. The importance of the use of water miscible cosolvents in transforming reactions from heterogeneous to homogeneous conditions as a potent medium engineering tool for protease-catalyzed oligopeptide synthesis is highlighted. For example, at 0.125 M l-Phe-Et.HCl, 20% (v/v) methanol, 18.6 mg/mL bromelain, in phosphate buffer (0.25M, pH 8), 40 degrees C, for 3 h, oligo(l-Phe) precipitated from the solution to yield 45 +/- 5%, in contrast, in the absence of cosolvent oligo(l-Phe) yield of 29 +/- 5% was obtained. The following reaction conditions were optimized for bromelain catalyzed oligo(l-Phe) synthesis: pH, temperature, substrate, enzyme, and cosolvent concentrations. DP(avg) and chain length distribution in the product peptides were investigated by (1)H NMR and MALDI-TOF.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP17585692	L-Phenylalanine hydrochloride solution		17585-69-2	Price

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