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Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00283
Biocatalysis in Organic Synthesis 1

1.4.5 Hydrolysis of Hydantoins, Dihydropyrimidines, and Related Compounds

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Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.

Authors: Asano, Y.; Babich, L.; Bertau, M.; Cobucci-Ponzano, B.; Díaz-Rodríguez, A.; Engel, U.; Faber, K.; Flitsch, S. L.; Glueck, S. M.; Gotor-Fernández, V.; Green, A. P.; Hall, M.; Hartog, A. F.; Hepworth, L. J.; Hollmann, F.; Jeromin, G. E.; Lauchli, R.; Lavandera, I.; Liese, A.; Martínková, L.; Moracci, M.; Pesci, L.; Rodríguez-Mata, M.; Rozzell, D.; Rudat, J.; Schmidberger, J. W.; Servi, S.; Slomka, C.; Syldatk, C.; Tasnádi, G.; Tessaro, D.; Veselá, A. B.; Voglmeir, J.; Wever, R.

Title: Biocatalysis in Organic Synthesis 1

Print ISBN: 9783131741318; Online ISBN: 9783131975218; Book DOI: 10.1055/b-003-125815

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

Providing advantages including high chemo-, regio-, and enantioselectivity as well as mild reaction conditions, biocatalytic reaction systems are becoming increasingly important for the synthesis of chiral fine chemicals. This chapter focuses on hydantoins and related compounds as promising substrates for the synthesis of optically pure amino acids and on the enzymes involved in these processes. In particular, the production of D-amino acids, such as D-4-hydroxyphenylglycine, via the so-called “hydantoinase process” is now well established. Many investigations regarding the synthesis of L-amino acids with the help of this process have also been carried out. A further interesting application is the synthesis of β-amino acids, which are gaining importance in the pharmaceutical industry due to their special structure. Different possibilities for the application of modified hydantoinase processes are discussed, in which dihydropyrimidines serve as substrates for β-amino acid synthesis. Moreover, various methods to improve the synthesis of amino acids are described.

Key words

hydantoins - dihydropyrimidines - hydrolysis - racemization - enantioselectivity - >N-carbamoylamino acids - hydantoinase process - amino acids - D-4-hydroxyphenylglycine - β-amino acids - directed evolution - whole-cell biocatalysis - immobilization - recombinant expression
 
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