Streptomyces lincolnensis Lincomycins

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 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. 

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. 

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... 

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. 

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. 

Prod, by Streptomyces lincolnensis with ethyl thiolincosaminide. Active against gram-positive bacteria. Cryst. +IH2O (as hydrochloride). [a]o +157 (H2O). N,S-Di-de-Me, N S-di-Et Lincomycin S. -Diethyllincomycin. U 25468. Antibiotic U 25468 [21085-65-4]... 

Lincomycin (63). The bio-origin of the methyl groups of lincomycin (63) was investigated with L-[Afe- H3]methionine. Addition of this labelled amino-acid to Streptomyces lincolnensis yielded a deuteriated antibiotic. The mass spectrum of this material showed molecular ions at m/e 406 (M + ), 409 (M -I- 3), 412 (Af + 6), and 415 (M + 9). This result, which agrees with a parallel study, indicated that a maximum of three CD3 groups were incorporated. 

Lincomycin is produced by Streptomyces lincolnensis var. lincolnensis in a number of culture media (Mason et al., 1962). It is active against a wide variety of primarily gram positive bacteria. Lincomycin was shown to have the structure in Fig. 1 by Hoeksema et aL (1964). The antibiotic contains two C9 fragments joined by an amidic linkage. One is ra> 5-l-methyl-4-propyl-L prohne which will be referred to as propylhygric acid (PHA). The other is methyl 6 amino-6,8-di-deoxy-1 -thio-D- ry Aro-a-D-galacto-octop5n anoside [methyl a-thiolincosaminide (MTL)] (Fig. 1). 

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