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Synthesis of biomimetic precursors of isovelleral analogues.

Röme, Daniel LU ; Arzel, Erwan; Johansson, Martin H LU and Sterner, Olov LU (2008) In ARKIVOC 6. p.91-99
Abstract
Based on how the mushroom Lactarius vellereus converts an inactive precursor into the cytotoxic dialdehyde isovelleral (1) via a cyclic enol ether, as part of a binary chemical defense system that protects the fruit bodies against parasites, a synthetic way to obtain analogous dialdehydes masked in the same way has been developed. As isovelleral analogues (e.g. 2 and 3) possess extremely potent cytotoxic activity, but display low selectivity as their biological activity is linked to their reactivity, suitably masked isovelleraloids that are converted to the corresponding dialdehyde under specific conditions, may constitute a way to utilize these potent compounds. Specifically, compounds 4 and 5, biomimetic precursors of the isovelleral... (More)
Based on how the mushroom Lactarius vellereus converts an inactive precursor into the cytotoxic dialdehyde isovelleral (1) via a cyclic enol ether, as part of a binary chemical defense system that protects the fruit bodies against parasites, a synthetic way to obtain analogous dialdehydes masked in the same way has been developed. As isovelleral analogues (e.g. 2 and 3) possess extremely potent cytotoxic activity, but display low selectivity as their biological activity is linked to their reactivity, suitably masked isovelleraloids that are converted to the corresponding dialdehyde under specific conditions, may constitute a way to utilize these potent compounds. Specifically, compounds 4 and 5, biomimetic precursors of the isovelleral analogues 2 and 3, but trapped as the stable methyl acetals, have been prepared. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Biomimetic, isovelleral analogues, cytotoxic dialdehyde, methyl acetal
in
ARKIVOC
volume
6
pages
91 - 99
publisher
Arkat USA Inc
external identifiers
  • WOS:000260410000009
  • Scopus:42249099624
ISSN
1424-6376
language
English
LU publication?
yes
id
7e48c81f-5238-494b-b481-b50c7129ab77 (old id 1214957)
alternative location
http://www.arkat-usa.org/get-file/23444/
date added to LUP
2008-08-14 16:02:08
date last changed
2016-10-13 04:46:41
@misc{7e48c81f-5238-494b-b481-b50c7129ab77,
  abstract     = {Based on how the mushroom Lactarius vellereus converts an inactive precursor into the cytotoxic dialdehyde isovelleral (1) via a cyclic enol ether, as part of a binary chemical defense system that protects the fruit bodies against parasites, a synthetic way to obtain analogous dialdehydes masked in the same way has been developed. As isovelleral analogues (e.g. 2 and 3) possess extremely potent cytotoxic activity, but display low selectivity as their biological activity is linked to their reactivity, suitably masked isovelleraloids that are converted to the corresponding dialdehyde under specific conditions, may constitute a way to utilize these potent compounds. Specifically, compounds 4 and 5, biomimetic precursors of the isovelleral analogues 2 and 3, but trapped as the stable methyl acetals, have been prepared.},
  author       = {Röme, Daniel and Arzel, Erwan and Johansson, Martin H and Sterner, Olov},
  issn         = {1424-6376},
  keyword      = {Biomimetic,isovelleral analogues,cytotoxic dialdehyde,methyl acetal},
  language     = {eng},
  pages        = {91--99},
  publisher    = {ARRAY(0xa157cf0)},
  series       = {ARKIVOC},
  title        = {Synthesis of biomimetic precursors of isovelleral analogues.},
  volume       = {6},
  year         = {2008},
}