Permetin A
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| Category | Antibiotics |
| Catalog number | BBF-02383 |
| CAS | 71888-70-5 |
| Molecular Weight | 1101.38 |
| Molecular Formula | C54H92N12O12 |
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Description
It is produced by the strain of Bacillus circulans AJ 3902. It's a peptide antibiotic. It has anti-gram-negative bacteria, gram-positive bacteria and anaerobic bacteria activity.
Specification
| Synonyms | Permycin A; 9-L-Serinepolypeptin A; Polypeptin A, 9-L-serine; Antibiotic NLF-II |
| IUPAC Name | 12,21,27-tris(2-aminoethyl)-18-benzyl-24,31-di(butan-2-yl)-3-(hydroxymethyl)-6,15-bis(2-methylpropyl)-9-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)CC)CCN |
| InChI | InChI=1S/C54H92N12O12/c1-11-32(9)42-27-43(68)58-35(18-21-55)47(70)66-45(33(10)12-2)53(76)60-36(19-22-56)46(69)62-40(26-34-16-14-13-15-17-34)51(74)61-38(24-29(3)4)49(72)59-37(20-23-57)48(71)65-44(31(7)8)52(75)63-39(25-30(5)6)50(73)64-41(28-67)54(77)78-42/h13-17,29-33,35-42,44-45,67H,11-12,18-28,55-57H2,1-10H3,(H,58,68)(H,59,72)(H,60,76)(H,61,74)(H,62,69)(H,63,75)(H,64,73)(H,65,71)(H,66,70) |
| InChI Key | NPQJTPHMCZYCNP-UHFFFAOYSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 1407.1°C at 760 mmHg |
| Density | 1.077 g/cm3 |
| Solubility | Soluble in potassium bromide |
Reference Reading
1. Isolation of a new peptide antibiotic, permetin A, from Bacillus circulans
Y Takahara, Y Takeuchi, I Komura, Y Hirose, S Murao J Antibiot (Tokyo). 1979 Feb;32(2):115-20. doi: 10.7164/antibiotics.32.115.
Permetin A was purified from the culture filtrate of Bacillus circulans AJ 3902 by extraction with n-butanol, precipitation with sodium helianthate, CM-cellulose column chromatography and Sephadex LH-20 column chromatography. The compound was found to be a new peptide antibiotic containing 2,4-diaminobutyric acid (Dab), leucine, isoleucine, phenylalanine, valine, serine (in a molar ratio of 3:2:1:1:1:1) and a fatty acid. This antibiotic showed activity in vitro against Gram-negative, Gram-positive and some anaerobic bacteria.
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.
3. The structure of permetin A, a new polypeptin type antibiotic produced by Bacillus circulans
Y Takeuchi, A Murai, Y Takahara, M Kainosho J Antibiot (Tokyo). 1979 Feb;32(2):121-9. doi: 10.7164/antibiotics.32.121.
The structure of permetin A(I), an antibiotic substance produced by Bacillus circulans AJ 3902, has been elucidated as a cyclic acyl peptide by means of the mass and nuclear magnetic resonance spectroscopic techniques. (Formula: see text.) The structure was found to be the same as polypeptin A(II) except that L-Thr in II is replaced by L-Ser in I. Details of the structural determination are given for the permetin A itself as well as for the hydrolyzed permetin A. (Formula: see text.)
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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 ╳
