A Chemoenzymatic Access to d- and l-Sphingosines Employing Hydroxynitrile Lyases

Autor:	Ulfried Felfer, Dean V. Johnson, Herfried Griengl
Rok vydání:	2000
Předmět:	food Chemistry Stereochemistry Yield (chemistry) Organic Chemistry Drug Discovery Prunus amygdalus Diastereomer Total synthesis Organic chemistry Enantiomer Biochemistry food.food
Zdroj:	Tetrahedron. 56:781-790
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)01024-8
Popis:	A chemoenzymatic access to d - or l -sphingosines is presented comprising of a total synthesis of the l - threo -isomer and formal syntheses of the other three isomers. Key to the development of a general synthetic strategy has been the use of enantiocomplementary hydroxynitrile lyases (Hnls) to yield an enantiomeric pair of starting materials. The ( S )-Hnl from Hevea brasiliensis has been used to prepare l - threo -sphingosine in 14 steps and an overall 12% yield. Application of the ( R )-Hnl from Prunus amygdalus formally allows synthesis of d - threo - and d - erythro -sphingosines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9e815d13fb081e0dff5a1c187ad62df5 https://doi.org/10.1016/s0040-4020(99)01024-8 Zobrazit plný text záznamu Full Text from ScienceDirect