38838-05-0Relevant articles and documents
Revisiting synthetic preparation of the quorum sensing substrate S-d-ribosyl-l-homocysteine (SRH)
Bolitho, Megan E.,Corcoran, Brendan J.,Showell-Rouse, Emily I.,Wang, Keeshia Q.
, p. 32 - 38 (2014)
Cleavage of the thioether bond of S-d-ribosyl-l-homocysteine (SRH) by the enzyme S-ribosylhomocysteinase (LuxS) serves as the final biosynthetic step in the generation of the quorum sensing autoinducer AI-2 by bacteria. Herein, a revised chemical synthesis of SRH is presented at convenient scale and purity for in vitro studies of LuxS. Potassium bis(trimethylsilyl)amide (KHMDS) is identified as a judicious base for the formation of the thioether of the target compound from readily-accessible precursors: a thiol nucleophile derived from l-homocystine and a sulfonate-activated d-ribosyl electrophile. The exclusive use of acid-labile protecting groups allows for facile deprotection to the final product, producing the TFA salt of SRH in five synthetic steps and 26% overall yield. The chemically-synthesized material is isolated at high purity and demonstrated to serve as the LuxS substrate by an in vitro assay.
Structure-property relationships of ribose based ionic liquids
Jopp, Stefan,Komabayashi, Mirai,Stiller, Tanja
, (2021/01/11)
The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.
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.