Periodate oxidation products of hydroxylysine in the synthesis of 5-substituted prolines

✍ Scribed by George Y. Wu; Sam Seifter

• Publisher: Elsevier Science
• Year: 1985
• Tongue: English
• Weight: 393 KB
• Volume: 147
• Category: Article
• ISSN: 0003-2697
• DOI: 10.1016/0003-2697(85)90014-4

✦ Synopsis

The amino acid hydroxylysine was subjected to oxidation by sodium metaperiodate under various conditions. It was found that in acid and high temperature, the initial oxidation product o-aminoglutaric -r-semialdehyde was converted to glutamic acid with a yield of 60%. The use of alkaline conditions of oxidation favored the cychzation of cr-aminoglutaric y-semialdehyde to form A'-pyrroline 5-carboxyhc acid. Addition of NaCN to this intermediate generated new prohne analogs, likely a mixture of cis-and trarr.s-5-cyanoprohnes, with a yield of 30%. Upon hydrolysis, the 5-cyanoprohnes were converted to a probable mixture of cis-and tram-S carboxyprohnes. Infrared and high-resolution mass spectral data of the analogs and visual absorption spectra of the ninhydrin products were obtained to confirm the structures. 0 198s Academic Press, Inc.