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Einfluß lipophiler Reste in Glucosaminderivaten auf deren Umsetzung durch Galactosyltransferase
Author(s) -
Áts SándorCsaba,
Lehmann Jochen
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940918
Subject(s) - chemistry , galactosyltransferase , pyranose , glucosamine , acylation , lipophilicity , ring (chemistry) , acceptor , steric effects , stereochemistry , medicinal chemistry , biochemistry , organic chemistry , catalysis , enzyme , physics , condensed matter physics
Influence of Lipophilic N ‐Acyl Derivatives of D ‐Glucosamine in the Galactosylation with Galactosyltransferase Several D ‐glucosamine derivatives varying in N ‐acylation were used as acceptor substrates for galactosyltransferase and the relative rates of their galactosylation by UDP‐Gal measured. One of them, 2‐deoxy‐2‐[4‐(2‐indolyl)butyramido]‐ D ‐glucose ( 6 ) was newly synthesised and galactosylated at a signficantly enhanced rate (14 times) in competition with GlcNAc as standard. Generally an increased lipophilicity increases the relative rate, provided the N ‐acyl group in question does not sterically hinder acceptor binding because it increases the bulk of the pyranose ring system.