Microbial degradation of deoxycholic acid by pseudomonas sp. ncib 10590. characterisation of products and a postulated pathway

✍ Scribed by R.F. Bilton; A.N. Mason; M.E. Tenneson

• Book ID: 104204507
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 520 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)88910-9

✦ Synopsis

3 one A ring structure. three acids 13.14 and IS shown by their spectra to have the 4 -en -3 -one A ring structure and two saturated keto acids 16 and 17. The chemical and spectroscopic propcrtks of I1 were almost identical with those of the acid 9. It was apparent from the UV, IR. PMR and mass spectra that the compounds had identical A ring structures. Treatment of I1 with acetic anftydride/pyridine gave a mono-acetate; oxidation of II with Jones' reagent' gave a ketone identical with 12. The JR (peak at 1704cm ") and PMR (2 proton multiplet at 2.7&2.5&S) spectra of 12 indicated that the ketone group was at C-12. The PMR spectrum of II (triplet at 3.986) indicated' a I2a-hydroxy group, a conclusion supported by the mass spectrum (intense M-18 peak). The mass spectrum of 11 also enabkd the kngth of the side chain to be determined: this mass spectrum and that of compound 9 both contained an intense peak at m/c 267. corresponding to the loss of the elements of water from the molecular ion and loss of the side chain by cleavage of the 17-20 bond." In the case of 11. the loss of 115 + 18 mass units indicated that the compound had an unchanged bile acid side chain. Its