کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1357822 981291 2014 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Enzymatic resolution of racemates with a ‘remote’ stereogenic center as an efficient tool in drug, flavor and vitamin synthesis
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Enzymatic resolution of racemates with a ‘remote’ stereogenic center as an efficient tool in drug, flavor and vitamin synthesis
چکیده انگلیسی

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.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry - Volume 22, Issue 20, 15 October 2014, Pages 5539–5546
نویسندگان
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