Carpetimycin A
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| Category | Antibiotics |
| Catalog number | BBF-00495 |
| CAS | 76025-73-5 |
| Molecular Weight | 342.37 |
| Molecular Formula | C14H18N2O6S |
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Description
It is produced by the strain of treptomyces griseus subsp. cryophilus, Str. sp. KC-6643. Carpetimycin is far more stable than Olivanic acid, and has very strong activity against gram-positive and negative bacteria (including β-lactamase producing bacteria). The activity of A is 8-32 times stronger than that of B. It has a strong inhibitory effect on β-lactamase.
Specification
| Related CAS | 76035-86-4 (sodium salt) |
| Synonyms | C 19393 H(2); C-19393 H(2); 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethenyl)sulfinyl)-6-(1-hydroxy-1-methylethyl)-7-oxo-, (5R-(3(R*(E)),5alpha,6beta))- |
| IUPAC Name | (5R,6R)-3-[(R)-[(E)-2-acetamidoethenyl]sulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| Canonical SMILES | CC(=O)NC=CS(=O)C1=C(N2C(C1)C(C2=O)C(C)(C)O)C(=O)O |
| InChI | InChI=1S/C14H18N2O6S/c1-7(17)15-4-5-23(22)9-6-8-10(14(2,3)21)12(18)16(8)11(9)13(19)20/h4-5,8,10,21H,6H2,1-3H3,(H,15,17)(H,19,20)/b5-4+/t8-,10+,23-/m1/s1 |
| InChI Key | FWWJFXYMDLTDNO-BBCPMLLOSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Melting Point | 145 °C(dec.) |
| Solubility | Soluble in Water |
Reference Reading
1. Oxazoline N-oxide mediated [2 + 3] cycloadditions. Application to a formal synthesis of (+)-carpetimycin A
M Mauduit, C Kouklovsky, Y Langlois, C Riche Org Lett. 2000 Apr 20;2(8):1053-6. doi: 10.1021/ol005596+.
[formula: see text] Cycloaddition between gamma,delta-unsaturated beta-enamino ester 9 and camphor-derived oxazoline N-oxide 8 afforded a single adduct, 14. Dipolarophile 9 proved to be very reactive despite the substitution on the double bond. Stereoselective sodium cyanoborohydride reduction of the imminium intermediate 14a gave rise stereoselectively to beta-amino ester derivative 15a. Oxidative acidic hydrolysis, oxidation of the resulting aldehyde 18, deprotection, and cyclization afforded the beta-lactam 23, a direct precursor of (+)-carpetimycin A.
2. Creation of novel chiral synthons with enzymes: application to enantioselective synthesis of antibiotics
M Ohno Ciba Found Symp. 1985;111:171-87. doi: 10.1002/9780470720929.ch12.
Retrosynthesis was carried out to generate, from a target molecule, a symmetric diester in the prochiral or meso form. The symmetric diester was subjected to asymmetric hydrolysis with pig liver esterase to create the corresponding chiral half-ester. The chiral half-ester was converted into the target molecule by organic synthesis. Thus, various types of carbapenem antibiotics, negamycin, showdomycin, 6-azapseudouridine, cordycepin, aristeromycin, neplanocin A, and precursors of fortimicin were efficiently synthesized with the desired absolute configuration. The methods for asymmetric synthesis starting from substrates with sigma-symmetry have been extensively developed.
3. Synthesis and structure-activity relationships of carbapenems related to C-19393 H2
H Natsugari, Y Matsushita, N Tamura, K Yoshioka, M Kondo, K Okonogi, M Kuno, M Ochiai J Antibiot (Tokyo). 1983 Jul;36(7):855-75. doi: 10.7164/antibiotics.36.855.
By applying the synthetic process reported in our previous paper, we synthesized new carbapenems having various (substituted) thio and alkoxy groups at the C(3) position and 1-hydroxy-1-methylethyl and analogous groups at the C(6) position with cis- and trans-stereochemistry; the in vitro antibacterial and beta-lactamase inhibitory activities of these new carbapenems were examined. Compared to C-19393 H2, some of these compounds (e.g., 11A-a-3 approximately 5) showed improved in vitro antibacterial activity especially against Pseudomonas aeruginosa; they showed a strong beta-lactamase inhibitory activity as well. Two noteworthy effects of substituent variation at the C(6) position on the activities were observed: 1) the trans-configuration caused a definite loss; and 2) introduction of 1-hydroxycyclobutyl and 1-hydroxy-1-methylpropyl groups in place of the 1-hydroxy-1-methylethyl group caused a diminution. The carbapenem (13A-a-2) with an alkoxy group at the C(3) position had a marked decrease in activity compared to the corresponding thio-substituted carbapenem (11A-a-12).
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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 ╳
