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Enzymatic resolution of racemates with a 'remote' stereogenic center as an efficient tool in drug, flavor and vitamin synthesis.

Abstract：

:The enantioselective recognition of 'remote' stereogenic centers represents a scientific task in organic chemistry being also of current interest in the pharmaceutical industry. This is due to a range of pharmaceutically relevant molecules or intermediates thereof bearing a stereogenic center, which is separated from the functional group by a larger non-chiral moiety such as, for example, a longer sequence of bonds of at least three carbon or hetero-atoms or by a planar aromatic moiety. Notably, biocatalysis turned out to provide an excellent solution for a range of challenging syntheses in this field. For example, efficient enzymatic resolution processes of racemates with such a 'remote' stereogenic center were developed for the synthesis of pelitrexol, lasofoxifene and (S)-monastrol. In general, good yields accompanied by high enantioselectivities were obtained, thus underlining the tremendous potential of enzymes to recognize and enantioselectively transform enantiomers of racemates with 'remote' stereogenic centers. Such or similar types of stereoselective recognitions of 'remote' stereogenic centers by means of enzymes have been also reported in the field of flavor and vitamin synthesis. Thus, biocatalysis represents a promising solution for the efficient approach to enantiomerically pure complex chiral molecules with stereogenic centers being located apart from the functional group, and it can be expected that enzymatic resolution will be increasingly applied when searching for an efficient and also technically feasible process for also novel complex chiral molecules bearing a 'remote' stereogenic center.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Alfaro Blasco M,Gröger H

doi

10.1016/j.bmc.2014.06.024

subject

Has Abstract

pub_date

2014-10-15 00:00:00

pages

5539-46

issue

20

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(14)00470-2

journal_volume

22

pub_type

杂志文章,评审

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