Cairomycin A
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| Category | Antibiotics |
| Catalog number | BBF-00196 |
| CAS | 78859-46-8 |
| Molecular Weight | 214.22 |
| Molecular Formula | C9H14N2O4 |
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Description
Cairomycin A is a peptide antibiotic produced by Streptomyces As-C-19, which has activity against gram-positive bacteria.
Specification
| Synonyms | 3,6-Dioxo-5-isopropyl-2-piperazineacetic acid; 2-Piperazineacetic acid, 5-(1-methylethyl)-3,6-dioxo-, (2S-cis)-; 2-Piperazineacetic acid, 3,6-dioxo-5-isopropyl-, (2S-cis)- |
| IUPAC Name | 2-[(2S,5S)-3,6-dioxo-5-propan-2-ylpiperazin-2-yl]acetic acid |
| Canonical SMILES | CC(C)C1C(=O)NC(C(=O)N1)CC(=O)O |
| InChI | InChI=1S/C9H14N2O4/c1-4(2)7-9(15)10-5(3-6(12)13)8(14)11-7/h4-5,7H,3H2,1-2H3,(H,10,15)(H,11,14)(H,12,13)/t5-,7-/m0/s1 |
| InChI Key | XPFDXOQLCBSANS-FSPLSTOPSA-N |
Properties
| Appearance | Yellow-brown Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 110-112°C |
Reference Reading
1. Isolation of cairomycins A and C
I R Shimi, S Fathey Antimicrob Agents Chemother. 1981 Jun;19(6):941-4. doi: 10.1128/AAC.19.6.941.
Cairomycin B in the fermentation broths of Streptomyces sp. strain AS-C-19 accompanied cairomycin A and cairomycin C. The cairomycins are peptides with potent activity against gram-positive bacteria. On acid hydrolysis, cairomycin A yielded valine and aspartic acid, whereas cairomycin C yielded lysine, glycine, valine, leucine, and aspartic acid, as identified by paper and gas chromatography. These amino acids were found to exist in their alpha-L form. Cairomycin A was tentatively assigned a 6-isopropyl-2,5-diketopiperazine-3-acetic acid structure. The three cairomycins were distinct from each other in their ultraviolet, infrared, and mass spectra; elemental analyses; and their chromatographic behavior in different developing solvents.
2. Four diastereoisomers of cyclo(-Asp-Val-): inconsistency of their properties with the proposed structure of cairomycin A
T Ueda, K Kiyohara, S Lee, H Aoyagi, N Izumiya J Antibiot (Tokyo). 1992 Feb;45(2):235-9. doi: 10.7164/antibiotics.45.235.
The four diastereoisomers of cyclo(-Asp-Val-) were synthesized to compare with a proposed structure of cairomycin A. Their antimicrobial activities were determined against both Gram-positive and Gram-negative bacteria. The physico-chemical properties of the isomers were characterized by mp, 1H NMR, IR, FAB-MS, and solubility in solvents, which were different from those reported for cairomycin A.
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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 ╳
