(2S)-4'-Depropyl-4'-propylidenelincomycin (Mixture of Diastereomers)

CAS: 37744-65-3

Ref. TR-D281915

Product Information

• Name: (2S)-4'-Depropyl-4'-propylidenelincomycin (Mixture of Diastereomers)
• Synonyms: Lincomycin EP Impurity B, Methyl 6,8-Dideoxy-6-[[[(2S)-1-methyl-4-propylidene-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-alpha-D-galacto-octopyranoside, Methyl (2S)-6,8-Dideoxy-6-[[(1-methyl-4-propylidene-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-erythro-alpha-D-galacto-octopyranoside, (S)-N-((1R,2R)-2-Hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylidenepyrrolidine-2-carboxamide, 4'-Depropyl-4'-propylidenelincomycin
• Brand: TRC

Description

Applications (2S)-4'-Depropyl-4'-propylidenelincomycin is an impurity of Lincomycin (L466200), an antibiotic produced by Streptomyces lincolnensis. Lincomycin is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA. Inhibits bacterial protein synthesis. Antibacterial.
References Mason, D.J., et al.: Antimicrob. Agents Chemother., 555 (1962); Gray, et al.: Toxicol. Appl. Pharmacol., 6, 476 (1964); Muti, H.Y., et al.: Anal. Profiles Drug Subs. Excip., 23, 269 (1994)

Chemical properties

• Molecular weight: 404.52
• Formula: C₁₈H₃₂N₂O₆S
• Color/Form: Neat
• InChI: InChI=1S/C18H32N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h6,9,11-16,18,21-24H,5,7-8H2,1-4H3,(H,19,25)/t9-,11+,12-,13+,14-,15-,16-,18-/m1/s1
• InChI key: InChIKey=UCVQMGJWVIGCAG-AYYBCBNYSA-N
• SMILES: CC/C=C1/C[C@@H](C(=O)N[C@H]([C@@H](C)O)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)N(C)C1