Streptomyces viridochromogenes

Bacillus thuringiensis, Streptomyces viridochromogenes Agrobacterium sp. strain CP4... 

Corn AgrEvo/1995 PAT Streptomyces viridochromogenes Tolerance to the herbicide glufosinate... 

Chacko et al. (1966) reported DDT dechlorinated to DDD by six actinomycetes Norcardiasp., Streptomyces albus, Streptomyces antibioticus, Streptomyces auerofaciens, Streptomyces cinna-moneus, Streptomyces viridochromogenes) but not by eight fungi. The maximum degradation observed was 25% in 6 d. 

In the framework of SFB380, two projects dealt extensively with acyloin-con-densing ThDP-dependent enzymes such as pyruvate decarboxylase (PDC), ben-zoylformate decarboxylase (BFD), or benzaldehyde lyase (BAL) (see Chapters 2.2.3 and 2.2.7). Another ThDP-dependent decarboxylase, phosphonopyruvate decarboxylase (PPD) from Streptomyces viridochromogenes, became available only recently and was studied in project B21. We wanted to find out whether this PDC-related enzyme could be a valuable tool in the provision of acyloin condensations involving C-P bonds (see Section 2.2.2.23). 

Avilamycins. At least 16 avilamycins have been reported. Avilamycins A (mp 181-182°C) and C (mp 188-189°C) are the primary components produced by the strain Streptomyces viridochromogenes. 

Avilamycin is produced from Streptomyces viridochromogenes NRRL 2860 ... 

Streptomyces hygroscopicus Streptomyces viridochromogenes Streptomyces roseosporus Streptomyces platensis Streptomyces fradiae... 

The partial assignment of the N NMR resonances of the thiopeptide antibiotic sulfomycin-I produced by Streptomyces viridochromogenes was reported <1998MRC635>. 

Avilamycins. At least 16 avilamycins have been reported (14,15,29) and are listed in Table 2. Avilamycins A (mp 181—182) and C (mp 188—189) are the primary components (14) produced by the strain Streptomyces viridochromogenes. Structures have been established based on chemical degradation, nmr, and x-ray analysis. Structures for the rest of the compounds have been assigned based on nmr and fab ms (14) interpretations. Avilamycins F and H have only one chlorine atom in the phenolic ring. Relative hplc retention times for all the avilamycins have been recorded (14). 

Streptazolin (600) is a lipophilic compound first isolated from Streptomyces viridochromogenes <81HCA1752, 82HCA1432). Because of the ease with which it polymerizes in concentrated form, its purification and characterization were made difficult. Its dihydro derivative (601) is a stable compound and exhibits antifungal activity. 

The enantioselective total synthesis of streptazolin (609), a neutral lipophilic antibiotic isolated from cultures of Streptomyces viridochromogenes, utilizes a tandem iminium ion— vinylsilane cyclization of the tartrate-derived 607 together with intramolecular acylation as a way of achieving high stereoselectivity. Heating a mixture of 570 and ( )-4-bromo-4-(tri-methylsilyl)-3-buten-l-amine (605) followed by dehydration with acetyl chloride provides the imide (606) in reproducible yields of 90%. Reduction of 606 with sodium borohydride affords 607, which is refluxed in trifluoroacetic acid to provide, after careful purification, the single bicyclic adduct 608 in 74% yield. This is then transformed in four steps to the desired streptazolin (609) [196] (Scheme 134). 

Poststatin, H-Val-Val-Pos-D-Leu-Val-OH, a naturally occurring 5-peptide isolated from Streptomyces viridochromogenes. It acts as an inhibitor of prolyl endopeptidase. Pos is the abbreviation for (S)-3-amino-2-oxopentanoic acid, named L-postine. The a-keto-amide group seems to be necessary for the biological activity [M. Tsuda et al., J. Antibiot.(Tokyo) 1996, 49, 1022 H. H. Wassermann, A. K. Petersen, Tetrahedron Lett. 1997, 38, 953]. 

C, H 3N03, Mr 207.23, amorphous, [0] +22° (CHCI3). A tricyclic oxazolidinone from cultures of Streptomyces viridochromogenes with a strong tendency for polymerization. 

In 1972 the team of Professor Zaehner at Tubingen described a Streptomyces strain producing a novel compound with antibiotic properties. The antibiotic tripeptide produced by Streptomyces viridochromogenes consists of two alanine residues and a novel amino acid that was named phosphinothricin [14] (Fig. 6.3.2). Owing to its structural analogy to glutamate Bayer et al. [14] tested and proved the hypothesis that phosphinothricin acts as an inhibitor of bacterial GS enzyme, whereas the tripeptide phosphinothricyl-alanyl.alanine did not inhibit the isolated GS enzyme. Nevertheless the tripeptide was 1.000-10.000-fold more active in its growth inhibitory effect on different bacteria. The discrepancy is explained by the observation that free phosphinothricin cannot be taken up efficiently by bacteria, whereas the tripeptide is taken up into the bacteria by peptide carriers and, subsequently, the tripeptide is cleaved. 

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