Scalable Synthesis of Human Ultralong Chain Ceramides

Ceramides with ultralong chains (≥30 carbons), also known as acylceramides, play a critical role in the survival of mammals on dry land. An efficient and scalable synthesis of four major classes of ultralong human skin ceramides is reported. The key approach involves the use of a succinimidyl ester...

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Bibliographic Details
Published in:Organic letters 2015-11, Vol.17 (21), p.5456-5459
Main Authors: Opálka, Lukáš, Kováčik, Andrej, Sochorová, Michaela, Roh, Jaroslav, Kuneš, Jiří, Lenčo, Juraj, Vávrová, Kateřina
Format: Article
Language:English
Subjects:
Animals
Ceramides - chemical synthesis
Ceramides - chemistry
Fatty Acids - chemical synthesis
Fatty Acids - chemistry
Humans
Molecular Structure
Skin - chemistry
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Summary:Ceramides with ultralong chains (≥30 carbons), also known as acylceramides, play a critical role in the survival of mammals on dry land. An efficient and scalable synthesis of four major classes of ultralong human skin ceramides is reported. The key approach involves the use of a succinimidyl ester that acts as a protective group, helps overcome the extremely low solubility, and simultaneously activates the fatty acid for its clean and high-yielding attachment to a sphingoid base.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02816