138328-64-0Relevant academic research and scientific papers
Arsenic-containing Ribosides from the Brown Alga Sargassum lacerifolium: X-Ray Molecular Structure of 2-Amino-3-propane-1-sulphonic Acid
Francesconi, Kevin A.,Edmonds, John S.,Stick, Robert V.,Skelton, Brian W.,White, Allan H.
, p. 2707 - 2716 (2007/10/02)
Three novel arsenic-containing ribosides, methyl 5-deoxy-5-(dimethylarsinoyl)-β-D-riboside, 1-O-mannitol, and a dimethylarsonio-β-D-riboside have been isolated from extracts of the brown alga Sargassum lacerifolium.In addition, five previously reported arsenic-containing ribosides, and some arsenate, were isolated from Sargassum, and dimethylarsinic acid was also shown to be present.The compounds were identified chiefly by NMR spectroscopy, and an X-ray molecular structure is reported for one of them, 2-amino-3-propane-1-sulphonic acid.The stereochemistry of the aglycones in these arsenic-containing ribosides is discussed and the configuration of 3--2-hydroxypropane-1-sulphonic acid 4 was assigned as 2S on the basis of a comparison of NMR spectra with those of synthetic model compounds.
The Synthesis of (R)-2',3'-Dihydroxypropyl 5-Deoxy-5-dimethylarsinyl-β-D-riboside, a Naturally Occurring Arsenic-Containing Carbohydrate
McAdam, David P.,Perera, Anna M. A.,Stick, Robert V.
, p. 1901 - 1908 (2007/10/02)
The synthesis of the title compound, isolated from the brown kelp (Ecklonia radiata) or the giant clam (Tridacna maxima), is reported.Glycosidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribose, either directly with (S)-1,2-di-O-benzylglycerol or via the derived orthoester with (S)-1,2-O-isopropylideneglycerol, led to two fully protected glycerol β-D-ribofuranosides.Subsequent chemical manipulations led to a common intermediate having a free hydroxy group at C 5 of the D-ribose residue.Replacement of this hydroxy group by a chlorine atom allowed the introduction of the dimethylarsinyl group at C 5 in a two-step procedure, and removal of protecting groups provided the natural product.
