14315-82-3Relevant articles and documents
Ectyoceramide, the first natural hexofuranosylceramide from the marine sponge Ectyoplasia ferox
Costantino, Valeria,Fattorusso, Ernesto,Imperatore, Concetta,Mangoni, Alfonso
, p. 1433 - 1437 (2003)
Ectyoceramide (1a), a unique monoglycosylceramide with a galactose in the furanose form, was isolated from Ectyoplasia ferox, and its structure was determined by NMR spectroscopy, multiple tandem mass spectrometry, and chemical degradation. Ectyoceramide is the first example of a monohexofuranosylceramide and, more generally, the first natural glycosphingolipid with its first sugar in the furanose form.
Blurring the boundary between bio- and geohopanoids: Plakohopanoid, a C32 biohopanoid ester from Plakortis cf. lita
Costantino, Valeria,Sala, Gerardo Della,Mangoni, Alfonso,Perinu, Cristina,Teta, Roberta
, p. 5171 - 5176 (2012/10/29)
Plakohopanoid (3a), a new type of hopanoid derivative composed of a C 32 hopanoid acid ester linked to a mannosyl-myo-inositol, was isolated from the sponge Plakortis cf. lita as its peracetyl derivative 3b. The structure of 3b was determined by a combination of spectroscopic analysis and micro-scale chemical degradation. Even though plakohopanoid was isolated from a sponge, its component parts are clearly of bacterial origin, and its bacterial biosynthesis is very likely. Until now, C32 hopanoic acids have been considered to be geohopanoids, i.e., diagenetic products that are formed through abiotic degradation of the biohopanoids present in bacteria. The presence of 3a in a marine living organism shows that there is a biosynthetic pathway to C32 hopanoic acids, and these substances should therefore no longer with certainty be considered to be geohopanoids. Copyright
Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters
Uriel, Clara,Ventura, Juan,Gomez, Ana M.,Lopez, J. Cristobal,Fraser-Reid, Bert
experimental part, p. 795 - 800 (2012/03/22)
Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.