BMY-28160
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| Category | Antibiotics |
| Catalog number | BBF-03254 |
| CAS | 94593-78-9 |
| Molecular Weight | 1087.35 |
| Molecular Formula | C53H90N12O12 |
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Description
BMY-28160 is an ester peptide antibiotic produced by Bacillus circulans H913-B4. It has anti-gram-positive bacteria, negative bacteria, anaerobic bacteria and fungi activity.
Specification
| Synonyms | Polypeptin A, 2-L-valine-9-L-serine- |
| IUPAC Name | 12,21,27-tris(2-aminoethyl)-18-benzyl-31-butan-2-yl-3-(hydroxymethyl)-6,15-bis(2-methylpropyl)-9,24-di(propan-2-yl)-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriacontane-2,5,8,11,14,17,20,23,26,29-decone |
| Canonical SMILES | CCC(C)C1CC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O1)CO)CC(C)C)C(C)C)CCN)CC(C)C)CC2=CC=CC=C2)CCN)C(C)C)CCN |
| InChI | InChI=1S/C53H90N12O12/c1-11-32(10)41-26-42(67)57-34(17-20-54)46(69)64-43(30(6)7)51(74)59-35(18-21-55)45(68)61-39(25-33-15-13-12-14-16-33)50(73)60-37(23-28(2)3)48(71)58-36(19-22-56)47(70)65-44(31(8)9)52(75)62-38(24-29(4)5)49(72)63-40(27-66)53(76)77-41/h12-16,28-32,34-41,43-44,66H,11,17-27,54-56H2,1-10H3,(H,57,67)(H,58,71)(H,59,74)(H,60,73)(H,61,68)(H,62,75)(H,63,72)(H,64,69)(H,65,70) |
| InChI Key | DTKPLFMHHIBZIK-UHFFFAOYSA-N |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi |
| Boiling Point | 1406.1±65.0°C at 760 mmHg |
| Melting Point | 225-229°C |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. Isolation and identification of lipopeptide antibiotics from Paenibacillus elgii B69 with inhibitory activity against methicillin-resistant Staphylococcus aureus
Rui Ding, Xue-Chang Wu, Chao-Dong Qian, Yi Teng, Ou Li, Zha-Jun Zhan, Yu-Hua Zhao J Microbiol. 2011 Dec;49(6):942-9. doi: 10.1007/s12275-011-1153-7. Epub 2011 Dec 28.
Two lipopeptide antibiotics, pelgipeptins C and D, were isolated from Paenibacillus elgii B69 strain. The molecular masses of the two compounds were both determined to be 1,086 Da. Mass-spectrometry, amino acid analysis and NMR spectroscopy indicated that pelgipeptin C was the same compound as BMY-28160, while pelgipeptin D was identified as a new antibiotic of the polypeptin family. These two peptides were active against all the tested microorganisms, including antibiotic-resistant pathogenic bacterial strains such as methicillin-resistant Staphylococcus aureus (MRSA). Time-kill assays demonstrated that pelgipeptin D exhibited rapid and effective bactericidal action against MRSA at 4×MIC. Based on acute toxicity test, the intraperitoneal LD50 value of pelgipeptin D was slightly higher than that of the structurally related antimicrobial agent polymyxin B. Pelgipeptins are highly potent antibacterial and antifungal agents, particularly against MRSA, and warrant further investigation as possible therapeutic agents for bacteria infections resistant to currently available antibiotics.
2. New Paenibacillus strain produces a family of linear and cyclic antimicrobial lipopeptides: cyclization is not essential for their antimicrobial activity
En Huang, Xu Yang, Liwen Zhang, Sun Hee Moon, Ahmed E Yousef FEMS Microbiol Lett. 2017 Apr 1;364(8). doi: 10.1093/femsle/fnx049.
A new bacterial isolate, Paenibacillus sp. OSY-N, showed potent antimicrobial activity against Gram-negative and Gram-positive bacteria. Antimicrobials produced by this strain were purified by reverse-phase high-performance liquid chromatography. Structural analysis, using mass spectrometry, of a single active HPLC fraction revealed two known cyclic lipopeptides (BMY-28160 and permetin A), a new cyclic lipopeptide, and the linear counterparts of these cyclic compounds. The latter were designated as paenipeptins A, B and C, respectively. The paenipeptins have not been reported before as naturally occurring products. Paenipeptins B and C differ at the acyl side chain; paenipeptin C contains a C8-, instead of C7-fatty acyl side chain. To demonstrate unequivocally the antimicrobial activity of the linear forms of this family of cyclic lipopeptides, analogs of the paenipeptins were synthesized chemically and their antimicrobial activity was tested individually. The synthetic linear lipopeptide with an octanoic acid side chain (designated as paenipeptin C') showed potent antimicrobial activity with minimum inhibitory concentrations of 0.5-4.0 μg/mL for Gram-negative and 0.5-32 μg/mL for Gram-positive bacteria. Findings demonstrated that peptide cyclization in this lipopeptide family is not essential for their antimicrobial activity. Most importantly, linear lipopeptides are more accessible than their cyclic counterparts through chemical synthesis.
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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 ╳
