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  • Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.

Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.

Journal of lipid research (2008-05-24)
Sarah T Pruett, Anatoliy Bushnev, Kerri Hagedorn, Madhura Adiga, Christopher A Haynes, M Cameron Sullards, Dennis C Liotta, Alfred H Merrill
ABSTRACT

"Sphingosin" was first described by J. L. W. Thudichum in 1884 and structurally characterized as 2S,3R,4E-2-aminooctadec-4-ene-1,3-diol in 1947 by Herb Carter, who also proposed the designation of "lipides derived from sphingosine as sphingolipides." This category of amino alcohols is now known to encompass hundreds of compounds that are referred to as sphingoid bases and sphingoid base-like compounds, which vary in chain length, number, position, and stereochemistry of double bonds, hydroxyl groups, and other functionalities. Some have especially intriguing features, such as the tail-to-tail combination of two sphingoid bases in the alpha,omega-sphingoids produced by sponges. Most of these compounds participate in cell structure and regulation, and some (such as the fumonisins) disrupt normal sphingolipid metabolism and cause plant and animal disease. Many of the naturally occurring and synthetic sphingoid bases are cytotoxic for cancer cells and pathogenic microorganisms or have other potentially useful bioactivities; hence, they offer promise as pharmaceutical leads. This thematic review gives an overview of the biodiversity of the backbones of sphingolipids and the broader field of naturally occurring and synthetic sphingoid base-like compounds.

MATERIALS
Product Number
Brand
Product Description

Avanti
1-deoxysphinganine, Avanti Research - A Croda Brand 860493P, powder
Avanti
N-C16-desoxymethylsphinganine, Avanti Research - A Croda Brand 860463P, powder
Avanti
1-desoxymethylsphinganine, Avanti Research - A Croda Brand 860473P, powder
Avanti
N-C24:1-deoxysphinganine, Avanti Research - A Croda Brand 860464P, powder
Avanti
N-C24:1-desoxymethylsphinganine, Avanti Research - A Croda Brand 860465P, powder
Avanti
4E,14Z-Sphingadiene, Avanti Research - A Croda Brand 860665P, powder
Avanti
Sphinganine (d20:0), Avanti Research - A Croda Brand 860674P, powder
Avanti
N-C12-desoxymethylsphinganine, N-lauroyl-1-desoxymethylsphinganine (m17:0/12:0), powder
Avanti
N-C12-deoxysphingosine, N-lauroyl-1-deoxysphingosine (m18:1/12:0), powder
Avanti
N-C16-deoxysphinganine, N-palmitoyl-1-deoxysphinganine (m18:0/16:0), powder
Avanti
N-C16-desoxymethylsphingosine, Avanti Research - A Croda Brand 860467P, powder
Avanti
N-C16-deoxysphingosine, N-palmitoyl-1-deoxysphingosine (m18:1/16:0), powder
Avanti
N-C24:1-deoxysphingosine, N-nervonoyl-1-deoxysphingosine (m18:1/24:1), powder
Avanti
N-C12-desoxymethylsphingosine, Avanti Research - A Croda Brand 860466P, powder
Avanti
N-C24:1-desoxymethylsphingosine, Avanti Research - A Croda Brand 860468P, powder