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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)
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author
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
2009-07-27 15:19:06
date last changed
2017-10-01 04:04:59
@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},
  volume       = {20},
  year         = {2009},
}