OA-6129 A
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| Category | Antibiotics |
| Catalog number | BBF-03306 |
| CAS | 82475-11-4 |
| Molecular Weight | 457.5 |
| Molecular Formula | C20H31N3O7S |
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Description
OA-6129 A is a carbapenem antibiotic produced by Streptomyces sp. OA-6129. It inhibits gram-positive, gram-negative bacteria and beta-lactamase.
Specification
| Synonyms | Antibiotic OA 6129A; OA 6129A; OA-6129A |
| IUPAC Name | (5R,6R)-3-[2-[3-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethylsulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| Canonical SMILES | CCC1C2CC(=C(N2C1=O)C(=O)O)SCCNC(=O)CCNC(=O)C(C(C)(C)CO)O |
| InChI | InChI=1S/C20H31N3O7S/c1-4-11-12-9-13(15(19(29)30)23(12)18(11)28)31-8-7-21-14(25)5-6-22-17(27)16(26)20(2,3)10-24/h11-12,16,24,26H,4-10H2,1-3H3,(H,21,25)(H,22,27)(H,29,30)/t11-,12-,16+/m1/s1 |
| InChI Key | AWQOXZYWBFPMRH-HSMVNMDESA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. Studies on the biosynthesis of carbapenem antibiotics. III. Enzymological characterization of the L-amino acid acylase activity of A933 acylase
K Kubo, T Ishikura, Y Fukagawa J Antibiot (Tokyo). 1985 May;38(5):622-30. doi: 10.7164/antibiotics.38.622.
A933 acylase, which is involved in exchange of the pantothenyl substituent of OA-6129 carbapenems with acetyl CoA, was characterized as an L-amino acid acylase with a molecular weight of 100,000 (+/- 8,000) and a pI value of 5.1. The highest L-amino acid acylase activity of A933 acylase was observed at 37 degrees C and pH 7 approximately 7.5 for N-chloroacetyl-L-phenylalanine. Unlike other amino acid acylases, A933 acylase was severely inhibited by cobalt ions and p-chloromercuribenzoate. The acylase also showed peptidase activity with some di- and tripeptides. A protein fraction with A933 L-amino acid acylase activity from blocked mutant 1501 lacked OA-6129A-depantothenylating activity.
2. Mutagenesis of OA-6129 carbapenem-producing blocked mutants and the biosynthesis of carbapenems
I Kojima, Y Fukagawa, M Okabe, T Ishikura, N Shibamoto J Antibiot (Tokyo). 1988 Jul;41(7):899-907. doi: 10.7164/antibiotics.41.899.
Streptomyces fulvoviridis A933 17M9 1501 is an A933 acylase-defective mutant derived from S. fulvoviridis A933 17M9 and thus produces the OA-6129 group of carbapenems and carbapenams. By further mutation of mutant 1501, 4 types of mutants (OA-6129 A + B1 + B2 producers; OA-6129 A + B2 producers; an OA-6129 A producer; non-producers) were obtained. The second type of mutant strains 4N 3607, 5NA 3949-40 and 5NE 252 proved useful for the fermentative production of carbapenem OA-6129 B2. These results of mutagenesis demonstrated that the sequence of carbapenem bioconversion in the horizontal route was hydroxylation at C-8----isomerization at C-6----sulfation at C-8 hydroxyl.
3. Microbial phosphorylation of the OA-6129 group of carbapenem compounds
K Kubo, T Ishikura, Y Fukagawa J Antibiot (Tokyo). 1985 Mar;38(3):333-9. doi: 10.7164/antibiotics.38.333.
The OA-6129 group of carbapenem antibiotics were phosphorylated with ATP by Brevibacterium ammoniagenes at the primary hydroxyl group of the C-3 pantetheinyl side chain. The phosphorylation resulted in the reduced antimicrobial activity against some Gram-positive bacteria, and the improved activity against some Gram-negative microbes. The increased resistance of the OA-6129 carbapenems due to phosphorylation was significant to mouse renal dehydropeptidase and moderate to the human enzyme. OA-6129A and B2 phosphates were found to be unsusceptible to A933 acylase, while OA-6129A and B2 were depantothenylated.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
