A21459 B
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| Category | Antibiotics |
| Catalog number | BBF-03131 |
| CAS | |
| Molecular Weight | 824.90 |
| Molecular Formula | C40H44N10O8S |
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Description
A21459 B 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 | A21459B |
| IUPAC Name | 4-(1H-indol-3-ylmethyl)-7-[(5-methoxy-1H-indol-3-yl)methyl]-13,18,22-trimethyl-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 | CC1C(=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/C40H44N10O8S/c1-20-35(53)46-22(3)40(57)50(4)18-34(52)45-21(2)39-49-32(19-59-39)38(56)48-31(12-23-15-41-28-9-7-6-8-26(23)28)37(55)47-30(36(54)43-17-33(51)44-20)13-24-16-42-29-11-10-25(58-5)14-27(24)29/h6-11,14-16,19-21,30-31,41-42H,3,12-13,17-18H2,1-2,4-5H3,(H,43,54)(H,44,51)(H,45,52)(H,46,53)(H,47,55)(H,48,56) |
| InChI Key | LMCHTEAQLRMIOY-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | mycoplasma |
| Boiling Point | 1380.7±0.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. 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.
2. 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.
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 ╳
