beta-Mannosidase and beta-hexosaminidase inhibitors: synthesis of 1,2-bis-epi-valienamine and 1-epi-2-acetamido-2-deoxy-valienamine from D-mannose
(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:
https://lup.lub.lu.se/record/1441859
- author
- Ramstadius, Clinton ; Hekmat, Omid LU ; Eriksson, Lars ; Stålbrand, Henrik LU and Cumpstey, Ian
- organization
- publishing date
- 2009
- 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}}, }