Methyl thiolincosaminide

Methyl thiolincosaminide (65), a carbohydrate component of the antibiotic lincomycin has been identified by n.m.r. An unusually... 

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. 

H). C,8H34N206S. the first lincosaminide antibiotic to which a structure was assigned, is defined chemically as methyl 6,8-dideoxy-6-(l-methyl-fro/M-4-propyl-L-pyrrolidin-2-ylcarbonylamino)-l-thio-D-erythro-L>-gal-actu-octopyranoside. Both lincomycin and the semisynthetic clindamycin (I, R = H, R = Cl), CisH ClNjOsS, are widely used in clinical practice. The trivial name of the sugar fragment of this antibiotic, methyl a-thiolincosaminide, has lent itself to the other members of this family, whether produced as secondary metabolites of soil microorganisms or derived semisynthetically by chemical modification. 

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... 

Thio, Me glycoside Methyl 6-amino-6,8-dideoxy-l-thio-D-eiyiYa o-a-D-g,z acXo-octopyranoside, 9CI, 8CI. Methyl a-thiolincosaminide [14810-93-6]... 

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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