Synthetic strategies for modified glycosphingolipids and their design as probes

CD Hunter, T Guo, G Daskhan, MR Richards… - Chemical …, 2018 - ACS Publications
The plasma membrane of cells contains a diverse array of lipids that provide important
structural and biological features. Glycolipids are typically a minor component of the cell …

Recent advances in the synthesis of sphingosine and phytosphingosine, molecules of biological significance

J Antonio Morales-Serna, J Llaveria… - Current Organic …, 2010 - ingentaconnect.com
Due to the relevant biological role of sphingosines, ceramides and glycosyl ceramides, and
the increasing demand of these compounds for biological evaluations, developing methods …

Lessons from nature: biomimetic organocatalytic carbon− carbon bond formations

D Enders, AA Narine - The Journal of organic chemistry, 2008 - ACS Publications
Nature utilizes simple C2 and C3 building blocks, such as dihydroxyacetone phosphate
(DHAP), phosphoenolpyruvate (PEP), and the “active aldehyde” in various enzyme …

Asymmetric Formal trans-Dihydroxylation and trans-Aminohydroxylation of α,β-Unsaturated Aldehydes via an Organocatalytic Reaction Cascade

Ł Albrecht, H Jiang, G Dickmeiss… - Journal of the …, 2010 - ACS Publications
This study demonstrates the first formal asymmetric trans-dihydroxylation and trans-
aminohydroxylation of α, β-unsaturated aldehydes in an organocatalytic multibond forming …

Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine

E Abraham, SG Davies, NL Millican… - Organic & …, 2008 - pubs.rsc.org
The highly diastereoselective anti-aminohydroxylation of α, β-unsaturated esters,
viaconjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl) amide and subsequent in …

Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH

RM Ndonye, DP Izmirian, MF Dunn… - The Journal of …, 2005 - ACS Publications
The phytosphingosine-containing α-galactosylceramides (α-GalCers), KRN7000 and OCH,
have been shown to activate NKT cells via interaction with CD1d, a member of the CD1 …

Preparation of anti-Vicinal Amino Alcohols: Asymmetric Synthesis of d-erythro-Sphinganine, (+)-Spisulosine, and d-ribo-Phytosphingosine

EDD Calder, AM Zaed… - The Journal of Organic …, 2013 - ACS Publications
Two variations of the Overman rearrangement have been developed for the highly selective
synthesis of anti-vicinal amino alcohol natural products. A MOM ether-directed palladium (II) …

Synthesis of γ-halogenated and long-chain β-hydroxy-α-amino acids and 2-amino-1, 3-diols using threonine aldolases

J Steinreiber, K Fesko, C Mayer, C Reisinger… - Tetrahedron, 2007 - Elsevier
The l-and d-threonine aldolase catalyzed formation of γ-halogenated and long-chain l-and d-
3-alkylserine-derivatives 1–12, respectively, was shown starting from glycine and …

High-yielding synthesis of sphingoid-type bases

C Séguin, F Ferreira, C Botuha, F Chemla… - The Journal of …, 2009 - ACS Publications
An efficient methodology for the synthesis of sphingoid-type bases is reported. It involves the
stereoselective addition of a racemic 3-alkoxy allenylzinc to enantiopure N-tert-butylsulfinyl …

Synthesis and structure-activity relationships of skin ceramides

J Novotny, A Hrabálek… - Current medicinal …, 2010 - ingentaconnect.com
Ceramides are a complex group of lipids that has gained much attention as cell signaling
molecules and skin barrier constituents. In the skin, these sphingolipids form a major part of …