Gaining insight into the catalysis by GH20 lacto-N-biosidase using small molecule inhibitors and structural analysis

被引：16

作者：

Hattie, Mitchell ^{[1
]}

Ito, Tasuku ^{[2
]}

Debowski, Aleksandra W. ^{[1
,3
]}

Arakawa, Takatoshi ^{[4
]}

Katayama, Takane ^{[5
]}

Yamamoto, Kenji ^{[6
]}

Fushinobu, Shinya ^{[4
]}

Stubbs, Keith A. ^{[1
]}

机构：

[1] Univ Western Australia, Sch Chem & Biochem, Crawley, WA 6009, Australia

[2] Natl Agr & Food Res Org, Natl Food Res Inst, Tsukuba, Ibaraki 3058642, Japan

[3] Univ Western Australia, Sch Pathol & Lab Med, Crawley, WA 6009, Australia

[4] Univ Tokyo, Dept Biotechnol, Bunkyo Ku, Tokyo 1138657, Japan

[5] Kyoto Univ, Grad Sch Biostudies, Kyoto 6068502, Japan

[6] Ishikawa Prefectural Univ, Res Inst Bioresources & Biotechnol, Nonoichi, Ishikawa 9218836, Japan

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 81期

基金：

澳大利亚研究理事会; 英国医学研究理事会;

关键词：

HUMAN-MILK OLIGOSACCHARIDES; SUBSTRATE-ASSISTED CATALYSIS; BIFIDOBACTERIUM-BIFIDUM; BETA-HEXOSAMINIDASE; TAY-SACHS; MECHANISM; CONSUMPTION; HYDROLASE; POTENT; RESISTANCE;

D O I：

10.1039/c5cc05494j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of potent inhibitors for lacto-N-biosidases and X-ray structural characterization of these compounds in complex with BbLNBase is described.

引用

页码：15008 / 15011

页数：4

共 40 条

[1] Variation of major neutral oligosaccharides levels in human colostrum [J].

Asakuma, S. ;

Urashima, T. ;

Akahori, M. ;

Obayashi, H. ;

Nakamura, T. ;

Kimura, K. ;

Watanabe, Y. ;

Arai, I. ;

Sanai, Y. .

EUROPEAN JOURNAL OF CLINICAL NUTRITION, 2008, 62 (04) :488-494

[2] Physiology of Consumption of Human Milk Oligosaccharides by Infant Gut-associated Bifidobacteria [J].

Asakuma, Sadaki ;

Hatakeyama, Emi ;

Urashima, Tadasu ;

Yoshida, Erina ;

Katayama, Takane ;

Yamamoto, Kenji ;

Kumagai, Hidehiko ;

Ashida, Hisashi ;

Hirose, Junko ;

Kitaoka, Motomitsu .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, 286 (40) :34583-34592

[3] SYNTHESIS OF 2-ACETAMIDO-2-DEOXY-D-GLUCONHYDROXIMOLACTONE-DERIVED AND CHITOBIONHYDROXIMOLACTONE-DERIVED N-PHENYLCARBAMATES, POTENTIAL INHIBITORS OF BETA-N-ACETYLGLUCOSAMINIDASE [J].

BEER, D ;

MALOISEL, JL ;

RAST, DM ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1990, 73 (07) :1918-1922

[4] APPLICATIONS OF NEXT-GENERATION SEQUENCING The human microbiome: at the interface of health and disease [J].

Cho, Ilseung ;

Blaser, Martin J. .

NATURE REVIEWS GENETICS, 2012, 13 (04) :260-270

[5] GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].

CREMER, D ;

POPLE, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358

[6] THE CHEMISTRY OF CASTANOSPERMINE .1. SYNTHETIC MODIFICATIONS AT C-6 [J].

FURNEAUX, RH ;

GAINSFORD, GJ ;

MASON, JM ;

TYLER, PC .

TETRAHEDRON, 1994, 50 (07) :2131-2160

[7] Novel substrate specificities of two lacto-N-biosidases towards β-linked galacto-N-biose-containing oligosaccharides of globo H, Gb5, and GA1 [J].

Gotoh, Aina ;

Katoh, Toshihiko ;

Sugiyama, Yuta ;

Kurihara, Shin ;

Honda, Yuji ;

Sakurama, Haruko ;

Kambe, Taiho ;

Ashida, Hisashi ;

Kitaoka, Motomitsu ;

Yamamoto, Kenji ;

Katayama, Takane .

CARBOHYDRATE RESEARCH, 2015, 408 :18-24

[8] Development of Tools to Study Lacto-N-Biosidase: An Important Enzyme Involved in the Breakdown of Human Milk Oligosaccharides [J].

Hattie, Mitchell ;

Debowski, Aleksandra W. ;

Stubbs, Keith A. .

CHEMBIOCHEM, 2012, 13 (08) :1128-1131

[9] Visualizing the Reaction Coordinate of an O-GlcNAc Hydrolase [J].

He, Yuan ;

Macauley, Matthew S. ;

Stubbs, Keith A. ;

Vocadlo, David J. ;

Davies, Gideon J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1807-+

[10] Crystal Structures of a Glycoside Hydrolase Family 20 Lacto-N-biosidase from Bifidobacterium bifidum [J].

Ito, Tasuku ;

Katayama, Takane ;

Hattie, Mitchell ;

Sakurama, Haruko ;

Wada, Jun ;

Suzuki, Ryuichiro ;

Ashida, Hisashi ;

Wakagi, Takayoshi ;

Yamamoto, Kenji ;

Stubbs, Keith A. ;

Fushinobu, Shinya .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2013, 288 (17) :11795-11806

← 1 2 3 4 →