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Lipase‐Mediated Purification of Methyl Nonactate, an Important Natural Product Building Block for Diversity‐Oriented Synthesis
Author(s) -
Dinges Jennifer M.,
Bessette Bradley A.,
Cox James E.,
Redder Casey R.,
Priestley Nigel D.
Publication year - 2006
Publication title -
biotechnology progress
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.572
H-Index - 129
eISSN - 1520-6033
pISSN - 8756-7938
DOI - 10.1021/bp0601138
Subject(s) - lipase , hydrolysis , streptomyces griseus , natural product , chemistry , fermentation , amino acid , organic chemistry , streptomyces , biochemistry , combinatorial chemistry , enzyme , bacteria , biology , genetics
Methyl nonactate is a valuable starting material for the production of natural product‐like combinatorial libraries and ketide amino acids, a series of novel conformationally constrained amino acid analogues. Fermentation of Streptomyces griseus generates high titers of macrotetrolide antibiotics from which methyl nonactate can be generated by methanolysis. Unfortunately, this approach generates mixtures of homologues that are not economically separable. We report a specific lipase‐mediated hydrolysis of nonactate derivatives that discriminates between homologues and is the foundation of an economically tractable preparation of methyl nonactate in scale.