Title: Carpetimycins
Literature References: Carbapenem antibiotics related to thienamycin and olivanic acids, q.q.v. Carpetimycins A, B, C and D are known. Prodn of A and B by Streptomyces strain No. C-19393, now named Streptomyces griseus subsp. cryophilus, and antibacterial properties: NL 8000628; A. Imada et al., US 4518529 (1980, 1985 to Takeda); A. Imada et al., J. Antibiot. 33, 1417 (1980); by Streptomyces strain KC-6643: M. Nakayama et al., ibid. 1388. Structure and abs config: S. Harada et al., J. Antibiot. 33, 1425 (1980); M. Nakayama et al., ibid. 34, 818 (1981). Mode of action study: Y. Nozaki et al., ibid. 206. Total synthesis of (±)-carpetimycin A: H. Natsugari et al., J. Chem. Soc. Perkin Trans. 1 1983, 403; M. Ihara et al., Heterocycles 20, 2182 (1983); J. D. Buynak, M. N. Rao, J. Org. Chem. 51, 1571 (1986). Synthesis of (-)-carpetimycin A: T. Iimori et al., J. Am. Chem. Soc. 105, 1659 (1983); M. Aratani et al., Tetrahedron Lett. 26, 223 (1985); M. Shibasaki et al., ibid. 2217.
Derivative Type: Carpetimycin A
CAS Registry Number: 76025-73-5
CAS Name: (5R,6R)-3-[(R)-[(1E)-2-(Acetylamino)ethenyl]sulfinyl]-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Additional Names: antibiotic Ab 651; antibiotic C-19393-H2; antibiotic KA-6643-A
Manufacturers' Codes: C-19393-H2
Molecular Formula: C14H18N2O6S
Molecular Weight: 342.37
Percent Composition: C 49.11%, H 5.30%, N 8.18%, O 28.04%, S 9.37%
Properties: Colorless solid, mp >145° (dec). [a]D24 -27° (c = 1.7 in water). uv max (water): 240, 288 nm (E1%1cm 369, 300) (Nakayama, 1980).
Melting point: mp >145° (dec)
Optical Rotation: [a]D24 -27° (c = 1.7 in water)
Absorption maximum: uv max (water): 240, 288 nm (E1%1cm 369, 300) (Nakayama, 1980)
Derivative Type: Carpetimycin B
CAS Registry Number: 76094-36-5
Additional Names: Antibiotic C-19393-S2; antibiotic KA-6643-B
Manufacturers' Codes: C-19393-S2
Molecular Formula: C14H18N2O9S2
Molecular Weight: 422.43
Percent Composition: C 39.81%, H 4.29%, N 6.63%, O 34.09%, S 15.18%
Properties: Colorless solid melting above 130° (dec). [a]D24 -145° (c = 1 in water). uv max (water): 240, 285 nm (E1%1cm 357, 305) (Nakayama, 1980).
Optical Rotation: [a]D24 -145° (c = 1 in water)
Absorption maximum: uv max (water): 240, 285 nm (E1%1cm 357, 305) (Nakayama, 1980)
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