Periodate oxidation products of hydroxylysine in the synthesis of 5-substituted prolines.
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 alpha-aminoglutaric gamma-semialdehyde was converted to glutamic acid with a yield of 60%. The use of alkaline conditions of oxidation favored the cyclization of alpha-aminoglutaric gamma-semialdehyde to form delta 1-pyrroline 5-carboxylic acid. Addition of NaCN to this intermediate generated new proline analogs, likely a mixture of cis- and trans-5-cyanoprolines, with a yield of 30%. Upon hydrolysis, the 5-cyanoprolines were converted to a probable mixture of cis- and trans-5-carboxyprolines. Infrared and high-resolution mass spectral data of the analogs and visual absorption spectra of the ninhydrin products were obtained to confirm the structures.
Wu
G Y
GY
Seifter
S
S
D006863:Hydrogen-Ion Concentration; D006901:Hydroxylysine; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D010504:Periodic Acid; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011758:Pyrroles / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D013696:Temperature
D011758:Pyrroles; D010504:Periodic Acid; C015485:delta-1-pyrroline-5-carboxylate; D006901:Hydroxylysine; D011392:Proline; C009288:metaperiodate