6R-(3,6-dideoxy-l-Arabino-Hexopyranosyloxy) heptanoic acid, preparation process for the same and dauer effect thereof
AssigneeKDR Biotech. Co. Ltd.
InventorsMankil Jung, Young Paik
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Abstract
The present invention relates to a determination of a stereochemistry, a synthesis and dauer effect of 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy)heptanoic acid as a pheromone isolated from the Caenorhabditis elegance related to suppress of aging and stress. It becomes possible to develop medical substances using the pheromone relating to aging, stress, metabolism, signal transfer system in vivo, and anti-cancer, obesity and a suppressing agent for aging and stress.
Claims14
A pheromone compound having a stereochemistry formula (I-1)
- where, X is H, alkali or alkali earth metal and n is 1-6 integer.
A pheromone intermediate having a formula (X).
- where, R1 is H, benzoyl or benzyl group.
A pheromone intermediate having a formula (XI).
- where, R2 is H, benzoyl or benzyl group.
A preparation method for a pheromone compound having a stereochemistry formula (I-1), the method comprising the steps of:
- acetalation of compound of formula (II) with compound of formula (III) in the presence of Lewis acid catalyst;
- converting an aliphatic terminal double bond of produced coupling reactant to an organic acid by an oxidant;
- and
- removing two O-benzoyl protecting group of deoxyrhamnosyl group by a base and acidifying by a acid.
- where, Bz is benzoyl or benzyl group.
A use of a pheromone compound of 6R-(3,6-dideoxy-L-arabino-hexopyranosyloxy)-heptanoic acid having a stereochemistry formula (I-1) and its alkali and alkali earth metal salts as medical agent for curing disease relating to aging and stress.
- where, X is H, alkali or alkali earth metal and n is 1-6 integer.
Dependencies are inferred from the claim text.