Cephabacin M1

Cephabacin M1

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Cephabacin M1
Category Antibiotics
Catalog number BBF-00534
CAS 99332-96-4
Molecular Weight 774.84
Molecular Formula C31H50N8O13S

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Description

It is produced by the strain of Lysobacter lactamgenus YK-90, Xanthomonas lactamgena YK-278、YK-280 and YK-431. It has anti-gram positive and negative bacterial activity. The Cephabacin M series is stable and has inhibitory effect on cephalosporin enzyme.

Specification

IUPAC Name (6R,7S)-7-[[(5R)-5-amino-5-carboxypentanoyl]amino]-3-[[6-amino-4-[[(2S)-1-[[(2S)-2,5-diaminopentanoyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-6-oxohexanoyl]oxymethyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES CC(C)C(C(=O)NC(=O)C(CCCN)N)NC(CC(=O)N)C(CC(=O)OCC1=C(N2C(C(C2=O)(NC(=O)CCCC(C(=O)O)N)OC)SC1)C(=O)O)O
InChI InChI=1S/C31H50N8O13S/c1-14(2)23(26(45)37-25(44)16(33)7-5-9-32)36-18(10-20(35)41)19(40)11-22(43)52-12-15-13-53-30-31(51-3,29(50)39(30)24(15)28(48)49)38-21(42)8-4-6-17(34)27(46)47/h14,16-19,23,30,36,40H,4-13,32-34H2,1-3H3,(H2,35,41)(H,38,42)(H,46,47)(H,48,49)(H,37,44,45)/t16-,17+,18?,19?,23-,30+,31-/m0/s1
InChI Key XCZVZZYVKNVEGK-JCAFXEPYSA-N

Properties

Appearance Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Solubility Soluble in Water

Reference Reading

1. Cephabacin M1-6, new 7-methoxycephem antibiotics of bacterial origin. I. A producing organism, fermentation, biological activities, and mode of action
Y Nozaki, N Katayama, S Tsubotani, H Ono, H Okazaki J Antibiot (Tokyo). 1985 Sep;38(9):1141-51. doi: 10.7164/antibiotics.38.1141.
New 7-methoxycephem antibiotics were found in culture filtrates of a bacterium isolated from a plant and named cephabacin M1-6. They are the first members of 7-methoxycephem antibiotics of bacterial origin. The producing organism was taxonomically characterized and identified as Xanthomonas lactamgena YK-431; other strains of this species have recently been reported to produce cephabacin F and H group antibiotics. Cephabacin M1-6 exhibited moderate antibacterial activity against Gram-negative and Gram-positive bacteria. Cephabacin M1-6 were as stable as cephamycin C to cephalosporinases. They showed inhibitory activity against a cephalosporinase of Proteus vulgaris GN 4413. The mode of action of cephabacin M1 was examined using Escherichia coli and Bacillus subtilis as test organisms; primary lethal targets of cephabacin M1 are penicillin-binding protein (PBP) 1 in E. coli and PBP 4 in B. subtilis.
2. Cephabacin M1-6, new 7-methoxycephem antibiotics of bacterial origin. II. Isolation, characterization and structural determination
S Tsubotani, T Hida, H Ono, S Harada J Antibiot (Tokyo). 1985 Sep;38(9):1152-65. doi: 10.7164/antibiotics.38.1152.
Six components of new cephem antibiotics, cephabacin M1-6, were isolated from the culture filtrate of Xanthomonas lactamgena YK-431 by various types of column chromatographies and preparative reverse-phase HPLC. Their structures were determined by spectroscopic analyses and degradation studies. They consist of 7-methoxydeacetylcephalosporin C as a nucleus and a tri- to heptapeptide including a new amino acid, which is bound at the 3-position with an ester bond.

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