Streptomyces lincolnensis

As described in U.S, Patent 3,086,912, the process comprises cultivating Streptomyces lincolnensis var. lincolnensis in an aqueous nutrient medium containing a source of assimilable carbohydrate and assimilable nitrogen under aerobic conditions until substantial activity is imparted to the medium by production of lincolnensin and isolating the lincol-nensin so produced. 

V-Demethyldindamycin /V-Demethyl-W- hydoroxymethyl clindamydn Streptomyces lincolnensis... 

Scheme 37. The flow of electrons in the N-oxide reductase system of Streptomyces lincolnensis. 

Macrolides, lincosamides and streptogramins are protein biosynthesis inhibitors that bind to 50S subunit of the ribosome and inhibit peptidyl tRNA translocation from the A-site to the P-site." Macrolides have a glycosylated 14-, 15- or 16-membered lactone ring structure and are produced by several species of Streptomyces. Lincosamide antibiotics were isolated initially from Streptomyces lincolnensis but later isolated from different species of Streptomcyces. Streptogramins were also isolated from Streptomycesgraminofaciens and subsequently from several different Streptomyces species. There are two structurally different streptogramins, A and B they are bacteriostatic individually and can be bactericidal when combined. 

Lincomycin Lincomycin, 6,8-dideoxy-6-fran -(l-methyl-4-propyl-L-2-pyrrolidincar-boxamido)-l-methylthio-D-eryf/2ro-a-D-gfl/flcfo-octopyranoside (32.5.1), is the first lincosamide that has found use in clinical practice, and which was isolated in 1962 from the culture liquid of the activity of the actinomycete Streptomyces lincolnensis [292-295]. 

Clindamycin is a chlorine-substituted derivative of lincomycin, an antibiotic that is elaborated by Streptomyces lincolnensis. 

Lincomydn is an antibiotic produced by Streptomyces lincolnensis. It is used in monopreparations or in combination with other antibiotics such as spectinomycin, sulfamethazine, and gentamicin, for the initial treatment of mild to moderate staphylococcal infections in a variety of animal species. It can be administered orally to poultry at dosages equivalent to up to 50 mg/kg hw/day for up to 7 days, and to swine at dosages equivalent to up to 10 mg/kg bw/day for up to 21 days. In calves, sheep, goats, and swine, it can be administered intramuscularly at dosages of up to 15 mg/kg bw/day for up to 4-7 days. It is also added in feeds for growth-promoting purposes. 

The antibiotic lincomycin (Figure 8.32) from Streptomyces lincolnensis bears a superficial similarity to the aminoglycosides, but has a rather more complex origin. The sugar fragment is termed methyl a-thiolincosaminide, contains a thiomethyl group, and is known to be derived... 

Clindamycin is a chlorine-substituted derivative of lincomycin, an antibiotic that is elaborated by Streptomyces lincolnensis. Lincomycin, although structurally distinct, resembles erythromycin in activity, but it is toxic and no longer used. 

A second typology of unsaturated carbapyranoses is represented by the rancinamycins, a group of secondary metabolites produced by Streptomyces lincolnensis, whose important antibiotic activity was... 

Lincocin lincomycin. lincomycin (ban. inn) (Lincocin ) is an antibiotic produced by Streptomyces lincolnensis and other S. spp. Clinically, it shows broad-spectrum antibacterial activity, lindane (ban. bsi. inn. iso. usan (gamma benzene hexachloride (ban) gamma-BHC Quellada ) is an insecticide. SCABICIDAL and PEDICULICIDAL AGENT. It can be used topically to treat parasitic infestation by mites and lice, linetastine (inn) (TMK 688) is a piperidinylethylpentadienyl derivative, a (5-) lipoxygenase INHIBITOR, an ANTIINFLAMMATORY with inhibitory effects in mouse skin tumour model. 

Lincomycin, an antibiotics produced by Streptomyces lincolnensis, has been used widely in the treatment of infections caused by gram positive organisms. Lincomycin inhibited microbial protein synthesis by interacting strongly and specifically with the 50 S ribosomal subunit at mutually related sites. The results show that such interaction was not influenced by any of the chemical modifications of lincomycin structure. One molecule of antibiotic bound per 50 S subunit. It inhibited peptide bond formation, a mixture of protein synthesis which was catalyzed by a peptidyl transferase centre on the 50 S subunit. It interfered with substrate binding at the P- or A- site on the catalytic centre. It probably bound to the ribosome in positions at or close to the peptide transferase centre. 

CAS 154-21-2. C18H34N206S. An antibacterial substance produced by Streptomyces lincolnensis. The hydrochloride is stable in the dry state and in aqueous solution for at least 24 months, soluble in water at room temperature in concentrations up to 500 mg/ mL. 

Biosynthesis. The terminal C-methyl of the propyl side chain, the L-methyl, and the ZV-methyl groups are derived from methionine (19). /ftmf-4-Propyl-L-proline [51101-27-6] was shown to accumulate when Streptomyces lincolnensis is grown in media deficient in sulfur, and the addition of L-tyrosine or L-dihydroxyphenylalanine (DOPA) was shown to stimulate this production. From a comparison of the incorporation of label from L-[l-14C]tyrosine and l[U-14C tyro sine, it was demonstrated that all of the carbon atoms of the propylproline other than the C-terminal methyl group were derived from tyrosine and, by the use of L-[15N]tyrosine, it was determined that the proline nitrogen atom was derived from the amino—nitrogen atom of tyrosine (20). 

Zhang, H-Z., Schmidt, H., and Piepersberg, W. (1992). Molecular cloning and characterization of two lincomycin-resistance genes, ImrA and ImrB, from Streptomyces lincolnensis 78-11. Mol. Microbiol. 6, 2147-2157. 

Lincomycin is a natural product isolated from fermentations of Streptomyces lincolnensis var. lincolnensis. It is active against Gram-positive organisms, including some anaerobes. It is indicated for the treatment of serious infections caused by sensitive strains of streptococci, pneumococci, and staphylococci. It generally is reserved for patients who are allergic to penicillin because of the increased risk of pseudomembranous colitis (described below). It also serves as the starting material for the synthesis of clindamycin (by a Sn-2 reaction that inverts the R stereochemistry of the C-7 hydroxyl to a C-7 S-chloride). 

The lincosamide class of antimicrobial drugs includes lincomycin, clindamycin, and pirlimycin two of these drugs—lincomycin and pirlimycin—are approved for use in food-producing species. Lincosamides are derivatives of an amino acid and a sulfur-containing galactoside. Lincomycin was isolated in 1962 from the fermentation product of Streptomyces lincolnensis subsp. lincolnensis. Clindamycin is a semi-synthetic derivative of lincomycin, and pirlimycin is an analog of clindamycin. 

A family of streptomycetes antibiotics from cultures of Streptomyces lincolnensis. Lincomycin is used clinically as a broad-spectrum antibiotic. It does not show any cross-resistance with other antibiotics but isolated cases of liver and kidney damage have been reported. For synthesis, see Ut.. The other members of the L. family also show biological activity against Gram-positive bacteria. 

CisHjaNjO S 406.542 Isol. from Streptomyces lincolnensis, Streptomyces espinosus and Streptomyces variabilis. Clinically used broad-spectrum antibiotic. Amorph. Sol. H2O, CHCI3, EtOAc, Mc2CO, butanol, MeOH fairly sol. Et20, C Hfc poorly sol. hexane [a]o +158 (c, 1 in H2O). pAa 7.5. Log P -0.12 (uncertain value) (calc). More stable in the salt form. 

C18H34N2O7S 422.542 From Streptomyces lincolnensis. Active against gram-positive and -negative bacteria. Log P -1.34 (uncertain value) (calc). 

C17H32N2O6S 392.516 From Streptomyces lincolnensis with methyl thiolincosaminide. Shows a broad spectrum of activity. Monohydrate (as hydrochloride), [a] +149 (c, 0.9 in H2O). H-De-Me, 3S-Et N-EthylUncomycin D. 

C19H36N2O6S 420.569 Prod, by Streptomyces lincolnensis with ethionine. Active against gram-positive bacteria. Monohydrate (as hydrochloride). [a]o +143 (H2O) (as hydrochloride). N,S-D/-de-Afe, S-Et Lincomydn K. 

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