Chlorocardicin
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| Category | Others |
| Catalog number | BBF-00306 |
| CAS | 95927-71-2 |
| Molecular Weight | 534.90 |
| Molecular Formula | C23H23ClN4O9 |
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Description
Chlorocardicin is produced by the strain of Strptomyces sp. Its structure and antibacterial activity are similar to those of Nocarcin A.
Specification
| Synonyms | 1-Azetidineacetic acid, 3-(((4-(3-amino-3-carboxypropoxy)phenyl)(hydroxyimino)acetyl)amino)-alpha-(3-chloro-4-hydroxyphenyl)-2-oxo-, (3S-(1(S*),3R*(Z(S*))))- |
| IUPAC Name | (2R)-2-amino-4-[4-[(E)-C-[[(3S)-1-[(R)-carboxy-(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid |
| Canonical SMILES | C1C(C(=O)N1C(C2=CC(=C(C=C2)O)Cl)C(=O)O)NC(=O)C(=NO)C3=CC=C(C=C3)OCCC(C(=O)O)N |
| InChI | InChI=1S/C23H23ClN4O9/c24-14-9-12(3-6-17(14)29)19(23(34)35)28-10-16(21(28)31)26-20(30)18(27-36)11-1-4-13(5-2-11)37-8-7-15(25)22(32)33/h1-6,9,15-16,19,29,36H,7-8,10,25H2,(H,26,30)(H,32,33)(H,34,35)/b27-18+/t15-,16+,19-/m1/s1 |
| InChI Key | UMDAIHWMUXNVSB-IMUCLJOZSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 221-224 °C |
Reference Reading
1. Chlorocardicin, a monocyclic beta-lactam from a Streptomyces sp. II. Isolation, physico-chemical properties and structure determination
J A Chan, E A Shultis, J J Dingerdissen, C W DeBrosse, G D Roberts, K M Snader J Antibiot (Tokyo). 1985 Feb;38(2):139-44. doi: 10.7164/antibiotics.38.139.
Chlorocardicin, a novel monocyclic beta-lactam, was isolated from the fermentation broth of a Streptomyces sp. by the use of non-ionic porous resin and reverse phase chromatography. This chlorine-containing antibiotic is structurally related to nocardicin A. Its physico-chemical characteristics and detailed NMR analysis are described.
2. Actinomycetes from the Red Sea Sponge Coscinoderma mathewsi: Isolation, Diversity, and Potential for Bioactive Compounds Discovery
Yara I Shamikh, Aliaa A El Shamy, Yasser Gaber, Usama Ramadan Abdelmohsen, Hashem A Madkour, Hannes Horn, Hossam M Hassan, Abeer H Elmaidomy, Dalal Hussien M Alkhalifah, Wael N Hozzein Microorganisms. 2020 May 23;8(5):783. doi: 10.3390/microorganisms8050783.
The diversity of actinomycetes associated with the marine sponge Coscinoderma mathewsi collected from Hurghada (Egypt) was studied. Twenty-three actinomycetes were separated and identified based on the 16S rDNA gene sequence analysis. Out of them, three isolates were classified as novel species of the genera Micromonospora, Nocardia, and Gordonia. Genome sequencing of actinomycete strains has revealed many silent biosynthetic gene clusters and has shown their exceptional capacity for the production of secondary metabolites, not observed under classical cultivation conditions. Therefore, the effect of mycolic-acid-containing bacteria or mycolic acid on the biosynthesis of cryptic natural products was investigated. Sponge-derived actinomycete Micromonospora sp. UA17 was co-cultured using liquid fermentation with two mycolic acid-containing actinomycetes (Gordonia sp. UA19 and Nocardia sp. UA 23), or supplemented with pure mycolic acid. LC-HRESIMS data were analyzed to compare natural production across all crude extracts. Micromonospora sp. UA17 was rich with isotetracenone, indolocarbazole, and anthracycline analogs. Some co-culture extracts showed metabolites such as a chlorocardicin, neocopiamycin A, and chicamycin B that were not found in the respective monocultures, suggesting a mycolic acid effect on the induction of cryptic natural product biosynthetic pathways. The antibacterial, antifungal, and antiparasitic activities for the different cultures extracts were also tested.
3. Chlorocardicin, a monocyclic beta-lactam from a Streptomyces sp. I. Discovery, production and biological activities
L J Nisbet, R J Mehta, Y Oh, C H Pan, C G Phelen, M J Polansky, M C Shearer, A J Giovenella, S F Grappel J Antibiot (Tokyo). 1985 Feb;38(2):133-8. doi: 10.7164/antibiotics.38.133.
Chlorocardicin is a new monocyclic beta-lactam produced by a Streptomyces sp. It is structurally related to nocardicin A but differs in having a m-chloro substituent on the p-hydroxyphenylglycine unit. The biological activity of chlorocardicin was similar to nocardicin A but the former showed less antagonism in complex media. Moderate in vitro activity was observed against Enterobacteriaceae and Pseudomonas aeruginosa. Chlorocardicin showed low activity against Staphylococcus aureus whereas nocardicin A was inactive. Both compounds were shown to be strongly potentiated by antibiotics that inhibit peptidoglycan biosynthesis and were antagonized by selected L- and D-amino acids.
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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 ╳
