Synthesis of biomimetic precursors of isovelleral analogues.
(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:
https://lup.lub.lu.se/record/1214957
- author
- Röme, Daniel LU ; Arzel, Erwan ; Johansson, Martin H LU and Sterner, Olov LU
- organization
- publishing date
- 2008
- 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
- 1551-7012
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 7e48c81f-5238-494b-b481-b50c7129ab77 (old id 1214957)
- alternative location
- http://www.arkat-usa.org/get-file/23444/
- date added to LUP
- 2016-04-04 11:36:12
- date last changed
- 2022-01-29 22:09:28
@article{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 = {{1551-7012}},
keywords = {{Biomimetic; isovelleral analogues; cytotoxic dialdehyde; methyl acetal}},
language = {{eng}},
pages = {{91--99}},
publisher = {{Arkat USA Inc}},
series = {{Arkivoc}},
title = {{Synthesis of biomimetic precursors of isovelleral analogues.}},
url = {{http://www.arkat-usa.org/get-file/23444/}},
volume = {{6}},
year = {{2008}},
}