Streptomyces griseolus

O Keefe DP, JA Romesser, KJ Leto (1988) Identification of constitutive and herbicide inducible cytochromes P-450 in Streptomyces griseolus. Arch Microbiol 149 406-412. 

Romesser JA, DP O Keefe (1986) Induction of cytochrome P-450-dependent sulfonylurea metabolism in Streptomyces griseolus. Biochem Biophys Res Comm 140 650-659. 

The transformation of sulfonylureas by Streptomyces griseolus grown in a complex medium containing glucose when the methyl group of the heterocyclic moieties is hydroxylated, and for some substrates, subsequently oxidized to the carboxylic acid (Romesser and O Keefe 1986 O Keefe et al. 1988). 

Sulfonylureas are the basis of a large group of herbicides. Cytochrome P450 enzymes in Streptomyces griseolus transform the sulfonylureas by hydroxylation (Omer et al. 1990) leaving the -SO2NHCONH- part of the structure unaltered (Harder et al. 1991). 

Omer CA, R Lenstra, PJ Little, C Dean, JM Tepperman, KJ Leto, JA Romesser, DP O Keefe (1990) Genes for two herbicide-inducible cytochromes P-450 from Streptomyces griseolus. J Bacterial 172 3335-3345. 

Streptomyces griseolus Streptomyces platensis Streptomyces rimosus Streptomyces roseochromogenus Streptomyces rimosus... 

Braatz JA, Bass MB, Omstein RL. An evaluation of molecular models of the cytochrome P450 Streptomyces griseolus enzymes P450SU1 and P450SU2. J Comput Aided Mol Des 1994 8 607-622. 

A swap of the methyl carbon with nitrogen in aza-AdoMet leads to sinefungin (see Fig. 2g)—a natural nucleoside antibiotic found in Streptomyces griseolus. Such reverse chemistry additionally enhances the chemical stability of cofactor. Because of the positive charge of the protonated amine and correct chirahty at the carbon center, sinefungin has an extremely high inhibitory potential for AdoMet-dependent methyltransferases. 

O Keefe, D.P., S.M.C. Lau, and P.A. Harder (1993). Efficiency and substrate-specificity of Streptomyces griseolus cytochrome P450SU1 and cytochrome P450SU2 monooxygenase reactions. Biochem. Soc. Trans. 21, 1073-1077. 

On feeding stereospecifically tritiated samples of ornithine to Streptomyces griseolus, it was found that the 5-pro-S hydrogen was lost on incorporation into sinefungin 274 so that bond formation was accompanied by inversion of configuration (282). 

Sinefungin is an adenine derivative, isolated from Streptomyces griseolus and it effectively inhibits VV mRNA (guanine-7-)methyltransferase and hence inhibits methylation of its mRNA [18]. 

CigHjgNOg, Mr 265.31, needles, mp. 144-145 °C, [a]o -30° (CH3OH). Isolated from Streptomyces griseolus. A. has antibacterial and antifungal properties and is active against tumors and protozoa. It inhibits protein biosynthesis. 

C15H23N7O5, Mr 381.39, amorphous, LD50 (mouse p. o.) 1000 mg/kg. An antiviral and antifungal nucleoside antibiotic from cultures of Streptomyces griseolus and S. incamatus. The development of S. as a fungicide, parasiticide, and human antimycotic was abandoned on account of its nephrotoxic side effects (see also nik-komycins, polyoxins). 

Sawada N, Sakaki T, Yoneda S, Kusudo T, Shinkyo R, Ohta M, Inouye K (2004) Conversion of vitamin D-3 to 1 alpha,25-dihydroxyvitamin D-3 by Streptomyces griseolus cytoehrome P450SU-1. Biochem Biophys Res Commun 320 156-164... 

Sugimoto H, Shinkyo R, Hayashi K, Yoneda S, Yamada M, Kamakura M, Ikushiro S-I, Shiro Y, Sakaki T (2008) Crystal structure of Streptomyces griseolus CYP105A1 catalyzing vitamin D hydroxylation. Vitamins (Kyoto) 82 497-502... 

C11H13N3O5 267.241 Nucleoside antibiotic. Identity with B 15645 not certain. Prod, by Micromo-nospora chalcea tubercidica and Streptomyces griseolus. Also isol. from the ascidian Aplidium pantherinum. Cytotoxic. Needles (H2O). 

C15H21N7O4 363.375 From Streptomyces griseolus and Strepto-myces incarnatus. Antifungal agent. 

Sawada, N., Sakaki, T, Yoneda, S., Kusudo, T, Shinkyo, R., Ohta, M., and Inouye, K. (2004) Conversion of vitamin D3 to lalpha,25-dihydroxyvitamin D3 by Streptomyces griseolus cytochrome P450SU-1. Biochcm. Bio-phys. Res. Commun., 320 (1), 156-164. 

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