Abstract
During the screening of microbial proline hydroxylases, novel proline 3-hydroxylase activities, which hydroxylate free l-proline to free cis-3-hydroxy-l-proline, were detected in whole cells of Streptomyces sp. strain TH1 and Bacillus sp. strains TH2 and TH3 from 3,000 strains isolated from soil. The reaction product was purified from a reaction mixture of Streptomyces sp. strain TH1, and its chemical structure was identified as cis-3-hydroxy-l-proline by instrumental analyses. Proline 3-hydroxylase activity was also detected in Streptomyces canus ATCC 12647 which produces the 3-hydroxyproline-containing peptide antibiotic telomycin. Bacillus sp. strains TH2 and TH3 were found to accumulate cis-3-hydroxy-l-proline in culture media at 426 and 352 (mu)M, respectively. It was suggested that hydroxylation occurred in a highly regio- and stereospecific manner at position 3 of l-proline because no hydroxylation product other than cis-3-hydroxy-l-proline was observed. Proline 3-hydroxylases of these strains were first characterized on crude enzyme preparations. Since 2-oxoglutarate and ferrous ion were required for hydroxylation of l-proline, these 3-hydroxylases were thought to belong to a family of 2-oxoglutarate-related dioxygenases. The reaction was inhibited by Co(sup2+), Zn(sup2+), and Cu(sup2+). l-Ascorbic acid accelerated the reaction. The optimum pH and temperature were 7.5 and 35(deg)C, respectively.
Full Text
The Full Text of this article is available as a PDF (271.0 KB).
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Adams E. Invertebrate collagens. Science. 1978 Nov 10;202(4368):591–598. doi: 10.1126/science.212833. [DOI] [PubMed] [Google Scholar]
- Cardinale G. J., Udenfriend S. Prolyl hydroxylase. Adv Enzymol Relat Areas Mol Biol. 1974;41(0):245–300. doi: 10.1002/9780470122860.ch6. [DOI] [PubMed] [Google Scholar]
- IRREVERRE F., MORITA K., ISHII S., WITKOP B. Occurrence of cis- and trans-3-hydroxy-L-proline in acid hydrolyzate of telomycin. Biochem Biophys Res Commun. 1962 Sep 25;9:69–71. doi: 10.1016/0006-291x(62)90089-x. [DOI] [PubMed] [Google Scholar]
- Katz E., Kamal F., Mason K. Biosynthesis of trans-4-hydroxy-L-proline by Streptomyces griseoviridus. J Biol Chem. 1979 Jul 25;254(14):6684–6690. [PubMed] [Google Scholar]
- Kuttan R., Radhakrishnan A. N. Biochemistry of the hydroxyprolines. Adv Enzymol Relat Areas Mol Biol. 1973;37:273–347. doi: 10.1002/9780470122822.ch5. [DOI] [PubMed] [Google Scholar]
- Lawrence C. C., Sobey W. J., Field R. A., Baldwin J. E., Schofield C. J. Purification and initial characterization of proline 4-hydroxylase from Streptomyces griseoviridus P8648: a 2-oxoacid, ferrous-dependent dioxygenase involved in etamycin biosynthesis. Biochem J. 1996 Jan 1;313(Pt 1):185–191. doi: 10.1042/bj3130185. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Lindblad W. J., Diegelmann R. F. Quantitation of hydroxyproline isomers in acid hydrolysates by high-performance liquid chromatography. Anal Biochem. 1984 May 1;138(2):390–395. doi: 10.1016/0003-2697(84)90827-3. [DOI] [PubMed] [Google Scholar]
- OGLE J. D., ARLINGHAUS R. B., LGAN M. A. 3-Hydroxyproline, a new amino acid of collagen. J Biol Chem. 1962 Dec;237:3667–3673. [PubMed] [Google Scholar]
- Onishi M., Okumura Y., Okamoto R., Ishikura T. Proline hydroxylation by cell free extract of a streptomycete. Biochem Biophys Res Commun. 1984 Apr 16;120(1):45–51. doi: 10.1016/0006-291x(84)91411-6. [DOI] [PubMed] [Google Scholar]
- Roach P. L., Clifton I. J., Fülöp V., Harlos K., Barton G. J., Hajdu J., Andersson I., Schofield C. J., Baldwin J. E. Crystal structure of isopenicillin N synthase is the first from a new structural family of enzymes. Nature. 1995 Jun 22;375(6533):700–704. doi: 10.1038/375700a0. [DOI] [PubMed] [Google Scholar]
- Shoji J., Hinoo H., Katayama T., Nakagawa Y., Ikenishi Y., Iwatani K., Yoshida T. Structures of new peptide antibiotics, plusbacins A1-A4 and B1-B4. J Antibiot (Tokyo) 1992 Jun;45(6):824–831. doi: 10.7164/antibiotics.45.824. [DOI] [PubMed] [Google Scholar]
- Staneck J. L., Roberts G. D. Simplified approach to identification of aerobic actinomycetes by thin-layer chromatography. Appl Microbiol. 1974 Aug;28(2):226–231. doi: 10.1128/am.28.2.226-231.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Wolff J. S., 3rd, Ogle J. D., Logan M. A. Studies on 3-methoxyproline and 3-hydroxyproline. J Biol Chem. 1966 Mar 25;241(6):1300–1307. [PubMed] [Google Scholar]