Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

beta-Mannosidase and beta-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from D-mannose

Ramstadius, Clinton ; Hekmat, Omid LU ; Eriksson, Lars ; Stålbrand, Henrik LU and Cumpstey, Ian (2009) In Tetrahedron: Asymmetry 20(6-8). p.795-807
Abstract
A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K-i 140 mu M. We report the crystal structures of three protected C-5=C-5a... (More)
A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K-i 140 mu M. We report the crystal structures of three protected C-5=C-5a unsaturated carbasugars with lyxo configuration. (C) 2009 Elsevier Ltd. All rights reserved. (Less)
Please use this url to cite or link to this publication:
author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron: Asymmetry
volume
20
issue
6-8
pages
795 - 807
publisher
Elsevier
external identifiers
  • wos:000266735500018
  • scopus:65549112847
ISSN
0957-4166
DOI
10.1016/j.tetasy.2009.02.016
language
English
LU publication?
yes
id
0bef56a0-c625-47c2-857b-f4aa4a3f8365 (old id 1441859)
date added to LUP
2016-04-01 13:13:20
date last changed
2022-01-27 18:02:04
@article{0bef56a0-c625-47c2-857b-f4aa4a3f8365,
  abstract     = {{A partially protected C-5=C-5a unsaturated carbasugar with alpha-lyxo configuration is synthesised in five steps and 26% overall yield from a known mannose-derived hemiacetal, using ring-closing metathesis as a key step. This carbasugar is converted into valienamine derivatives with beta-lyxo (i.e., corresponding to beta-manno at C-1-C-4), alpha-lyxo (i.e., corresponding to alpha-manno at C-1-C-4) and beta-2-acetamido-2-deoxy-xylo (i.e., corresponding to beta-GlcNAc at C-1-C-4) configurations. This is the first report of the synthesis of the beta-lyxo compound, 1,2-bis-epi-valienamine, which was found to inhibit Cellulomonas fimi beta-mannosidase (CfMan2A) with K-i 140 mu M. We report the crystal structures of three protected C-5=C-5a unsaturated carbasugars with lyxo configuration. (C) 2009 Elsevier Ltd. All rights reserved.}},
  author       = {{Ramstadius, Clinton and Hekmat, Omid and Eriksson, Lars and Stålbrand, Henrik and Cumpstey, Ian}},
  issn         = {{0957-4166}},
  language     = {{eng}},
  number       = {{6-8}},
  pages        = {{795--807}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron: Asymmetry}},
  title        = {{beta-Mannosidase and beta-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from D-mannose}},
  url          = {{http://dx.doi.org/10.1016/j.tetasy.2009.02.016}},
  doi          = {{10.1016/j.tetasy.2009.02.016}},
  volume       = {{20}},
  year         = {{2009}},
}