Mechanistic insights into glycosidase chemistry

被引:329
作者
Vocadlo, David J. [1 ]
Davies, Gideon J. [2 ]
机构
[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
[2] Univ York, Dept Chem, Struct Biol Lab, York YO10 5YW, N Yorkshire, England
基金
加拿大健康研究院; 加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/j.cbpa.2008.05.010
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The enzymatic hydrolysis of the glycosidic bond continues to gain importance, reflecting the critically important roles complex glycans play in health and disease as well as the rekindled interest in enzymatic biomass conversion. Recent advances include the broadening of our understanding of enzyme reaction coordinates, through both computational and structural studies, improved understanding of enzyme inhibition through transition state mimicry and fascinating insights into mechanism yielded by physical organic chemistry approaches.
引用
收藏
页码:539 / 555
页数:17
相关论文
共 120 条
[31]  
JONES CS, 1980, J BIOL CHEM, V255, P1861
[32]   Mechanism of class 1 (Glycosylhydrolase family 47) α-mannosidases involved in N-glycan processing and endoplasmic reticulum quality control [J].
Karaveg, K ;
Siriwardena, A ;
Tempel, W ;
Liu, ZJ ;
Glushka, J ;
Wang, BC ;
Moremen, KW .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (16) :16197-16207
[33]   Structural basis of the inhibition of Golgi α-mannosidase II by mannostatin A and the role of the thiomethyl moiety in ligand-protein interactions [J].
Kawatkar, Sameer P. ;
Kuntz, Douglas A. ;
Woods, Robert J. ;
Rose, David R. ;
Boons, Geert-Jan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) :8310-8319
[34]   NAG-thiazoline, an N-acetyl-beta-hexosaminidase inhibitor that implicates acetamido participation [J].
Knapp, S ;
Vocadlo, D ;
Gao, ZN ;
Kirk, B ;
Lou, JP ;
Withers, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (28) :6804-6805
[35]   Enzymatic polymerization to artificial hyaluronan: A novel method to synthesize a glycosaminoglycan using a transition state analogue monomer [J].
Kobayashi, S ;
Morii, H ;
Itoh, R ;
Kimura, S ;
Ohmae, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11825-11826
[36]   Synthesis of artificial chitin: Irreversible catalytic behavior of a glycosyl hydrolase through a transition state analogue substrate [J].
Kobayashi, S ;
Kiyosada, T ;
Shoda, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13113-13114
[37]   The active site of cellobiohydrolase Cel6A from Trichoderma reesei:: The roles of aspartic acids D221 and D175 [J].
Koivula, A ;
Ruohonen, L ;
Wohlfahrt, G ;
Reinikainen, T ;
Teeri, TT ;
Piens, K ;
Claeyssens, M ;
Weber, M ;
Vasella, A ;
Becker, D ;
Sinnott, ML ;
Zou, JY ;
Kleywegt, GJ ;
Szardenings, M ;
Ståhlberg, J ;
Jones, TA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10015-10024
[38]   STEREOCHEMISTRY AND THE MECHANISM OF ENZYMATIC REACTIONS [J].
KOSHLAND, DE .
BIOLOGICAL REVIEWS OF THE CAMBRIDGE PHILOSOPHICAL SOCIETY, 1953, 28 (04) :416-436
[39]   Probing the transition states of four glucoside hydrolyses with 13C kinetic isotope effects measured at natural abundance by NMR spectroscopy [J].
Lee, JK ;
Bain, AD ;
Berti, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3769-3776
[40]   Detailed dissection of a new mechanism for glycoside cleavage:: α-1,4-glucan lyase [J].
Lee, SS ;
Yu, S ;
Withers, SG .
BIOCHEMISTRY, 2003, 42 (44) :13081-13090