Structural Formula Vector Image
Title: Thienamycin
CAS Registry Number: 59995-64-1
CAS Name: (5R,6S)-3-[(2-Aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Molecular Formula: C11H16N2O4S
Molecular Weight: 272.32
Percent Composition: C 48.52%, H 5.92%, N 10.29%, O 23.50%, S 11.77%
Literature References: The first member of a family of des-thia-carbapenem nucleus antibiotics having a thioethylamine side-chain on the enamine portion of the fused 5-membered ring. Produced by Streptomyces cattleya: J. S. Kahan et al., US 3950357 (1976 to Merck & Co.). Discovery, isoln, taxonomy, physical properties: eidem, J. Antibiot. 32, 1 (1979). Structure, absolute configuration: G. Albers-Schönberg et al., J. Am. Chem. Soc. 100, 6491 (1978). Synthesis of the (±)-form: D. B. R. Johnston et al., ibid. 313; F. A. Bouffard et al., J. Org. Chem. 45, 1130 (1980); S. M. Schmitt et al., ibid. 1135, 1142; D. G. Melillo et al., Tetrahedron Lett. 21, 2783 (1980); eidem, ibid. 22, 913 (1981); M. Shiozaki, T. Hiraoka, Tetrahedron 38, 3457 (1982). Alternate prepn of key intermediate: J. D. Buynak et al., Chem. Commun. 1986, 941. Stereocontrolled synthesis of the naturally occurring (+)-form: T. Salzmann et al., J. Am. Chem. Soc. 102, 6161 (1980); S. Karady et al., ibid. 103, 6765 (1981). Alternate synthetic routes: S. T. Hodgson et al., Tetrahedron 41, 5871 (1985); T. Iimori, M. Shibasaki, Tetrahedron Lett. 26, 1523 (1985); T. Chiba, T. Nakai, ibid. 4647; D. J. Hart, D. C. Ha, ibid. 5493; T. Kametani et al., J. Org. Chem. 50, 2327 (1985); H. Maruyama, T. Hiraoka, ibid. 51, 399 (1986); D. G. Melillo et al., ibid. 1498. Continuous production in immobilized cell systems: E. J. Arcuri et al., Biotechnol. Bioeng. 28, 842 (1986). Biosynthesis: J. M. Williamson et al., J. Biol. Chem. 260, 4637 (1985). In vitro antibacterial activity: F. P. Tally et al., Antimicrob. Agents Chemother. 14, 436 (1978); S. S. Weaver et al., ibid. 15, 518 (1979). Evaluation of in vitro and in vivo activities: H. Kropp et al., Antimicrob. Agents Chemother. 17, 993 (1980). Comparative study vs gram-positive and gram-negative aerobic and anaerobic species and b-lactamase stability: H. C. Neu, P. Labthavikul, ibid. 21, 180 (1982). N-Acyl derivatives as anti-inflammatory agents: J. B. Doherty et al., US 4465687 (1984 to Merck & Co.). Pharmacokinetics, bacteriological efficacy: P. Patamasucon, G. H. McCracken, Antimicrob. Agents Chemother. 21, 390 (1982). Review of early syntheses of the carbapenems: T. Kametani, Heterocycles 17, 463-506 (1982).
Properties: White hygroscopic solid. [a]D27 +82.7° (c = 1.0 in water). uv max (water, pH 4-8): 296.5 nm (e 7900); (pH 2): 309 nm; (pH 12): 300.5 nm. Freely sol in water, sparingly sol in methanol. In dilute soln, stability is optimal between pH 6-7, declining with unusual rapidity above that range. Susceptible to inactivation by dilute solns of hydroxylamine and cysteine.
Optical Rotation: [a]D27 +82.7° (c = 1.0 in water)
Absorption maximum: uv max (water, pH 4-8): 296.5 nm (e 7900)
Derivative Type: N-Formimidoylthienamycin monohydrate see Imipenem

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