A21459 A
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| Category | Antibiotics |
| Catalog number | BBF-03130 |
| CAS | |
| Molecular Weight | 838.93 |
| Molecular Formula | C41H46N10O8S |
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Description
A21459 A is a cyclic peptide antibiotic produced by Actinoplanes sp. It has anti-clostridium (MIC 0.03-8 μg/mL) and mycoplasma (MIC 2 μg/mL) activity.
Specification
| Synonyms | A21459A |
| IUPAC Name | 13-ethyl-4-(1H-indol-3-ylmethyl)-7-[(5-methoxy-1H-indol-3-yl)methyl]-18,22-dimethyl-16-methylidene-24-thia-3,6,9,12,15,18,21,26-octazabicyclo[21.2.1]hexacosa-1(25),23(26)-diene-2,5,8,11,14,17,20-heptone |
| Canonical SMILES | CCC1C(=O)NC(=C)C(=O)N(CC(=O)NC(C2=NC(=CS2)C(=O)NC(C(=O)NC(C(=O)NCC(=O)N1)CC3=CNC4=C3C=C(C=C4)OC)CC5=CNC6=CC=CC=C65)C)C |
| InChI | InChI=1S/C41H46N10O8S/c1-6-28-37(55)46-22(3)41(58)51(4)19-35(53)45-21(2)40-50-33(20-60-40)39(57)49-32(13-23-16-42-29-10-8-7-9-26(23)29)38(56)48-31(36(54)44-18-34(52)47-28)14-24-17-43-30-12-11-25(59-5)15-27(24)30/h7-12,15-17,20-21,28,31-32,42-43H,3,6,13-14,18-19H2,1-2,4-5H3,(H,44,54)(H,45,53)(H,46,55)(H,47,52)(H,48,56)(H,49,57) |
| InChI Key | PSBVOIWKVJOOJJ-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | mycoplasma |
| Boiling Point | 1375.2±65.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Antibiotics A21459 A and B, new inhibitors of bacterial protein synthesis. I. Taxonomy, isolation and characterization
E Selva, L Gastaldo, G S Saddler, G Toppo, P Ferrari, G Carniti, B P Goldstein J Antibiot (Tokyo). 1996 Feb;49(2):145-9. doi: 10.7164/antibiotics.49.145.
Novel cyclic peptide antibiotics A21459 A and B are produced by a member of the genus Actinoplanes sp. These antibiotics inhibit bacterial protein synthesis and have selective antimicrobial activity against clostridia, mycoplasma and some Gram-negative bacteria.
2. Argyrins, immunosuppressive cyclic peptides from myxobacteria. II. Structure elucidation and stereochemistry
Larissa Vollbrecht, Heinrich Steinmetz, Gerhard Hofle, Lukas Oberer, Grety Rihs, Günter Bovermann, Peter von Matt J Antibiot (Tokyo). 2002 Aug;55(8):715-21. doi: 10.7164/antibiotics.55.715.
The structures of argyrins A-H were elucidated by NMR spectroscopy, chemical degradation and X-ray analysis as cyclic octapeptides. Argyrins A and B, in addition to the common amino acids tryptophan, glycine, dehydroalanine and alanine or alpha-aminobutyric acid, sarcosine, contain 2-(1-aminoethyl)thiazol-4-caboxylic acid and the novel amino acid 4'-methoxytryptophan. In argyrins C and D the latter is replaced by 4'-methoxy 2'-methyltryptophan. According to NMR analysis the solution and crystal conformations of argyrins A and B are identical in CDCl3 and slightly different in acetone-d6. Argyrins A and B are identical with the antibiotics A21459 A and B, whose structures are revised with respect to 4'-methoxytryptophan.
3. Antibiotics A21459 A and B, new inhibitors of bacterial protein synthesis. II. Structure elucidation
P Ferrari, K Vékey, M Galimberti, G G Gallo, E Selva, L F Zerilli J Antibiot (Tokyo). 1996 Feb;49(2):150-4. doi: 10.7164/antibiotics.49.150.
The structures of the antibiotics, active against a few Gram-negative bacteria and Clostridium difficile, were determined on the basis of physicochemical analyses on the intact molecules and on the acid hydrolysate of A21459 A. FAB-MS and 1H and 13C NMR investigations identified the amino acid units and determined their sequence. Antibiotics A21459 A and B are homodetic cyclic peptides constituted by eight amino acid units. They are glycine, methoxytryptophan, tryptophan, cysteine, alanine, sarcosine, dehydroalanine, and alpha-aminobutyric acid for A21459 A (alanine for A21459 B). Cysteine and alanine condensed to form a thiazole moiety, according to the biosynthesis of thiazole containing antibiotics.
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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 ╳
