13552-09-5Relevant articles and documents
Antifungal activity of bifunctional sphingolipids. Intramolecular synergism within long-chain alpha,omega-bis-aminoalcohols.
Nicholas, Gillian M,Li, Ronghua,MacMillan, John B,Molinski, Tadeusz F
, p. 2159 - 2162 (2002)
The in vitro antifungal activity of a series of alpha,omega-bifunctionalized aminoalcohols against Candida glabrata was measured. The dimeric bi-functionalized lipids exhibited activity about approximately 10-fold higher higher than D-sphingosine, which is a larger factor than expected from the simple additive effects of vicinal aminoalcohols groups.
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Grob,Jenny
, p. 2106,2110 (1952)
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Grob et al.
, p. 2249,2250m 2252 (1951)
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Newman
, p. 100,102 (1974)
Convergent evolution of bacterial ceramide synthesis
Ashley, Ben,Campopiano, Dominic J.,Chamberlain, Joshua D.,Coleman, Aimiyah,D’Emilia, Rachel,Fu, Larina,Guan, Ziqiang,Hansen, Matthew E. B.,Klein, Eric A.,Mohan, Eric C.,Nguyen, Hung,Stankeviciute, Gabriele,Tang, Peijun
, (2022/01/06)
The bacterial domain produces numerous types of sphingolipids with various physiological functions. In the human microbiome, commensal and pathogenic bacteria use these lipids to modulate the host inflammatory system. Despite their growing importance, their biosynthetic pathway remains undefined since several key eukaryotic ceramide synthesis enzymes have no bacterial homolog. Here we used genomic and biochemical approaches to identify six proteins comprising the complete pathway for bacterial ceramide synthesis. Bioinformatic analyses revealed the widespread potential for bacterial ceramide synthesis leading to our discovery of a Gram-positive species that produces ceramides. Biochemical evidence demonstrated that the bacterial pathway operates in a different order from that in eukaryotes. Furthermore, phylogenetic analyses support the hypothesis that the bacterial and eukaryotic ceramide pathways evolved independently. [Figure not available: see fulltext.]
Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine
Zhou, Yubai,Mukherjee, Munmun,Gupta, Anil K.,Wulff, William D.
, p. 2230 - 2233 (2017/05/12)
All four stereoisomers of sphinganine can be synthesized by a multicomponent aziridination of an aldehyde, an amine and an α-diazo carbonyl compound mediated by a BOROX catalyst with high asymmetric induction (≥96% ee). The threo isomers are available from ring-opening of cis-aziridines by an oxygen nucleophile with inversion at the C-3 position and the erythro-isomers are likewise available from trans-aziridines.
