OA-6129 D
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| Category | Antibiotics |
| Catalog number | BBF-03310 |
| CAS | 85414-25-1 |
| Molecular Weight | 475.6 |
| Molecular Formula | C20H33N3O8S |
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Description
OA-6129 D is a carbapenem antibiotic produced by Streptomyces sp. OA-6129. It inhibits gram-positive, gram-negative bacteria and beta-lactamase. It is also effective against dehydrodipeptidase and Comamonas terrigena B-996.
Specification
| Synonyms | Antibiotic OA 6129D; OA 6129D; OA-6129D |
| IUPAC Name | (2S,3S,5R,6R)-3-[2-[3-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethylsulfanyl]-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| Canonical SMILES | CC(C1C2CC(C(N2C1=O)C(=O)O)SCCNC(=O)CCNC(=O)C(C(C)(C)CO)O)O |
| InChI | InChI=1S/C20H33N3O8S/c1-10(25)14-11-8-12(15(19(30)31)23(11)18(14)29)32-7-6-21-13(26)4-5-22-17(28)16(27)20(2,3)9-24/h10-12,14-16,24-25,27H,4-9H2,1-3H3,(H,21,26)(H,22,28)(H,30,31)/t10?,11-,12+,14+,15-,16+/m1/s1 |
| InChI Key | IDHUQZYNJINFBS-VWLVWCDXSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. Studies on the biosynthesis of carbapenem antibiotics. I. Biosynthetic significance of the OA-6129 group of carbapenem compounds as the direct precursors for PS-5, epithienamycins A and C and MM 17880
Y Fukagawa, M Okabe, S Azuma, I Kojima, T Ishikura, K Kubo J Antibiot (Tokyo). 1984 Nov;37(11):1388-93. doi: 10.7164/antibiotics.37.1388.
Based on the working hypothesis that the OA-6129 group of carbapenem compounds might be the direct precursors for PS-5, epithienamycins A and C and MM 17880, Streptomyces fulvoviridis A933 17M9, a producer of PS-5, PS-6, PS-7, PS-8, epithienamycins A, B, C and D, MM 17880, MM 13902 and MM 4550, was subjected to NTG-mutation to provide a blocked mutant numbered 1501 which was found to produce OA-6129 A, OA-6129B1, OA-6129B2 and OA-6129C instead of PS-5, epithienamycins A and C and MM 17880, respectively. In a cell-free system, the parent strain demonstrated an ability to convert OA-6129A to NS-5, whereas the mutant did not. The L- and D-amino acid acylases were also shown to depantothenylate the OA-6129 group of carbapenems.
2. Studies on the biosynthesis of carbapenem antibiotics. II. Isolation and functions of a specific acylase involved in the depantothenylation of the OA-6129 compounds
K Kubo, T Ishikura, Y Fukagawa J Antibiot (Tokyo). 1984 Nov;37(11):1394-402. doi: 10.7164/antibiotics.37.1394.
A specific acylase designated A933 acylase was isolated and purified to 90% protein homogeneity from Streptomyces fulvoviridis A933 17M9 which produces PS-5, epithienamycins A and C and MM 17880 together with minor carbapenem analogs, penicillin N and cephamycin C. This enzyme was found to catalyze the depantothenylation of OA-6129 carbapenems; the acyl exchange of OA-6129 carbapenems with acyl CoA's; the deacetylation of N-acetyl-L-amino acids; and the acylation of NS-5 and 6-aminopenicillanate with acyl CoA's, whereas the deacetylation of PS-5 and N-acetyl-D-amino acids; and the deacylation of benzylpenicillin and cephalosporin C were not observed. Similar enzyme activities were also detected in Streptomyces cattleya, Streptomyces cremeus subsp. auratilis and Streptomyces argenteolus which are all carbapenem producers.
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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 ╳
