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One‐Pot Oxidation–Hydrocyanation Sequence Coupled to Lipase‐Catalyzed Diastereoresolution in the Chemoenzymatic Synthesis of Sugar Cyanohydrin Esters (Eur. J. Org. Chem. 14/2012)
Author(s) -
Hietanen Ari,
Kanerva Liisa T.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201290033
Subject(s) - chemistry , lipase , cyanohydrin , hydrocyanation , nitrile , organic chemistry , stereoselectivity , burkholderia , catalysis , stereochemistry , enzyme , bacteria , biology , genetics
Abstract The cover picture shows the key intermediates in the chemoenzymatic sequence in one‐pot from peracetylated methyl α‐ D ‐glycosides into sugar cyanohydrin acetates. The method allows the stereoselective substitution of hydrogen with a nitrile group through labile intermediates that are not separated. Lipase from Burkholderia cepacia , a key enzyme responsible for selectivity in the sequence, is shown in the middle (adopted from pdb entry 1OIL). Details are discussed in the article by A. Hietanen and L. T. Kanerva on p. 2729 ff.