Synthesis and chromatographic properties of 1,3-thiazane-2-carboxylic acid (beta-homothiaproline).
Details are reported for the synthesis of 1,3-thiazane-2-carboxylic acid, or beta-homothiaproline, 3-Bromopropylamine is allowed to react with sodium thiosulfate to give S-sulfo-homocysteamine, which is then split in acidic medium to homocystamine. Homocystamine is reduced by a slight excess of dithioerythritol and allowed to react with sodium glyoxylate. beta-Homothiaproline is then isolated by ion exchange on Dowex 50 and finally obtained in pure crystalline form, with a fairly good yield. Some chemical and chromatographic properties of beta-homothiaproline, in comparison with gamma-homothiaproline (1,3-thiazane-4-carboxylic acid), beta-thiaproline (thiazolidine-2-carboxylic acid) and gamma-thiaproline (thiazolidine-4-carboxylic acid) are described.
D000603:Amino Acids, Sulfur / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002852:Chromatography, Ion Exchange; D002855:Chromatography, Thin Layer; D003538:Cystamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013843:Thiazines / Q000138:chemical synthesis*
D000603:Amino Acids, Sulfur; D013843:Thiazines; C029174:homocystamine; C029175:1,3-thiazine-2-carboxylic acid; D003538:Cystamine