Docking and molecular dynamics studies on the stereoselectivity in the enzymatic synthesis of carbohydrates

• Tipo: Artigo em Revista Científica Internacional
• Data: 2009

Autores

Natercia F Bras (Autor) Outra; Pedro A Fernandes (Autor) FCUP; Maria J Ramos (Autor) FCUP

Revista

Título: Theoretical Chemistry Accounts

Vol. 122

Páginas: 283-296

ISSN: 1432-881X

Editora: Springer Nature

Indexação

ISI Web of Knowledge - 15 Citações

Scopus - 16 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: P-003-MCY

DOI: 10.1007/s00214-009-0507-2

Abstract (EN): Glycosidases constitute a vast family of enzymes that catalyze the breaking and formation of glycosidic bonds. The synthesized oligosaccharides, being crucial to life, are involved in many biochemical processes, particularly in the pharmaceutical and food industries. The proposed catalytic mechanism of retaining glycoside hydrolases (glycosidases) occurs via a double displacement mechanism involving a covalent glycosyl enzyme intermediate. During the transglycosylation reactions, the control of the stereoselectivity for the formation of the new bond remains a complicated problem in the chemical synthesis of oligosaccharides. In this paper, docking and molecular dynamics methods were used to study the second step of the mechanism of transglycosylation in retaining glycosidases from six microorganisms with known stereoselectivity. Using the natural substrates as donor and acceptor molecules, we were able to corroborate and provide structural information about the active site, the trapped monosaccharide acceptor and the bound intermediates during the step that precedes transglycosylation, as well as identify and understand the commonly displayed stereoselectivity by these glycosidases in nature. The information obtained with this procedure helps to recognize, explain and predict the stereoselectivity of the sugars studied. These kind of procedures can be used to improve the efficiency of large-scale industrial synthesis of a specific sugar.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 14