Document Detail


Multicomponent Synthesis of Ugi-type Ceramide Analogues and Neoglycolipids from Lipidic Isocyanides.
MedLine Citation:
PMID:  22533639     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Unique types of ceramide and glycolipid architectures were obtained by means of Ugi reactions incorporating lipidic isocyanides as surrogates of sphingolipids. The multicomponent nature of this process allowed for a highly efficient assembly process, wherein two of the components provided the lipidic tails while a third one incorporated either the functionality suitable for the conjugation to sugar or the sugar moiety itself. Two dissimilar strategies were implemented: i) the initial assembly of ceramide analogues followed by glycosylation to produce a glycolipid skeleton and ii) the one-pot construction of glycolipid frameworks by condensation of lipidic isocyanides either with lipidic amines and oligosaccharidic acids or with fatty acids and oligosaccharidic amines. Whereas both approaches are amenable for accessing analogues of anticancer glycolipids, the latter one proved greater potential owing to its more straightforward and efficient character. Overall, the methodology developed shows great promise toward the massive - eventually combinatorial - production of neoglycolipids suitable for biological screening.
Authors:
Karell Pérez-Labrada; Ignacio Brouard; Inmaculada Méndez; Daniel García Rivera
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-4-25
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2012 Apr 
Date Detail:
Created Date:  2012-4-26     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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