Synthesis of neoglycosphingolipid from methoxyamino-functionalized ceramide

被引：10
作者：
Ishida, Junya [1 ,2 ]
Hinou, Hiroshi [1 ,2 ,3 ]
Naruchi, Kentaro [3 ]
Nishimura, Shin-Ichiro [1 ,2 ,3 ]
机构：
[1] Hokkaido Univ, Grad Sch Life Sci, Kita Ku, Sapporo, Hokkaido 0010021, Japan
[2] Hokkaido Univ, Fac Adv Life Sci, Kita Ku, Sapporo, Hokkaido 0010021, Japan
[3] Med Chem Pharmaceut Co Ltd, Sapporo, Hokkaido 0010021, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 04期
关键词：
Neoglycosphingolipid; Ceramide; Oxime; Acyl migration; Glycoblotting; ACID; OLIGOSACCHARIDE; LINKAGE; ENDOGLYCOCERAMIDASE; GLYCOSIDASE; CLEAVES; DESIGN;
D O I：
10.1016/j.bmcl.2013.12.091
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
An efficient approach for the synthesis of a methoxyamino- functionalized ceramide was established from phytosphingosine using specific Nb -> Na acyl migration of the octadecanoyl group during the removal of Na-Fmoc protective group. One step glycoblotting reaction of the ceramide mimic with lactose afforded a neoglycosphingolipid showing potent inhibitory activity against recombinant endoglycoceramidase II from Rhodococcus sp. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1197 / 1200
页数：4
相关论文
共 44 条
[1]   Design of a covalently bonded glycosphingolipid microarray [J].
Arigi, Emma ;
Blixt, Ola ;
Buschard, Karsten ;
Clausen, Henrik ;
Levery, Steven B. .
GLYCOCONJUGATE JOURNAL, 2012, 29 (01) :1-12
[2]   The structural basis of glycosidase inhibition by five-membered iminocyclitols:: The clan a glycoside hydrolase endoglycoceramidase as a model system [J].
Caines, Matthew E. C. ;
Hancock, Susan M. ;
Tarling, Chris A. ;
Wrodnigg, Tanja M. ;
Stick, Robert V. ;
Stuetz, Arnold E. ;
Vasella, Andrea ;
Withers, Stephen G. ;
Strynadka, Natalie C. J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4474-4476
[3]   Structural and mechanistic analyses of endo-glycoceramidase II, a membrane-associated family 5 glycosidase in the Apo and GM3 ganglioside-bound forms [J].
Caines, Matthew E. C. ;
Vaughan, Mark D. ;
Tarling, Chris A. ;
Hancock, Susan M. ;
Warren, R. Antony J. ;
Withers, Stephen G. ;
Strynadka, Natalie C. J. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, 282 (19) :14300-14308
[4]   2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid, an amino acid for the synthesis of mimics of O-linked glycopeptides [J].
Carrasco, MR ;
Brown, RT ;
Doan, VH ;
Kandel, SM ;
Lee, FC .
BIOPOLYMERS, 2006, 84 (04) :414-420
[5]   Synthesis and Preclinical Evaluation of QS-21 Variants Leading to Simplified Vaccine Adjuvants and Mechanistic Probes [J].
Chea, Eric K. ;
Fernandez-Tejada, Alberto ;
Damani, Payal ;
Adams, Michelle M. ;
Gardner, Jeffrey R. ;
Livingston, Philip O. ;
Ragupathi, Govind ;
Gin, David Y. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (32) :13448-13457
[6]   An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells [J].
Cheng, Janice M. H. ;
Chee, Stephanie H. ;
Knight, Deborah A. ;
Acha-Orbea, Hans ;
Hermans, Ian F. ;
Timmer, Mattie S. M. ;
Stocker, Bridget L. .
CARBOHYDRATE RESEARCH, 2011, 346 (07) :914-926
[7]   GLYCOLIPID FUNCTION [J].
CURATOLO, W .
BIOCHIMICA ET BIOPHYSICA ACTA, 1987, 906 (02) :137-160
[8]   Combinatorial synthesis of MUC1 glycopeptides: Polymer blotting facilitates chemical and enzymatic synthesis of highly complicated mucin glycopeptides [J].
Fumoto, M ;
Hinou, H ;
Ohta, T ;
Ito, T ;
Yamada, K ;
Takimoto, A ;
Kondo, H ;
Shimizu, H ;
Inazu, T ;
Nakahara, Y ;
Nishimura, SI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11804-11818
[9]   Enhancing the Divergent Activities of Betulinic Acid via Neoglycosylation [J].
Goff, Randal D. ;
Thorson, Jon S. .
ORGANIC LETTERS, 2009, 11 (02) :461-464
[10]   Designer enzymes for glycosphingolipid synthesis by directed evolution [J].
Hancock, Susan M. ;
Rich, Jamie R. ;
Caines, Matthew E. C. ;
Strynadka, Natalie C. J. ;
Withers, Stephen G. .
NATURE CHEMICAL BIOLOGY, 2009, 5 (07) :508-514
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