Bacitracin A (8CI) Peptides Bacitracin A is a homodetic cyclic peptide consisting of (4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid attached head-to-tail to L-leucyl,D-glutamyl, L-lysyl, D-ornityl, L-isoleucyl, D-phenylalanyl, L-histidyl. D-aspartyl and L-asparaginyl residues coupled in sequence and cyclised by condensation of the side-chain amino group of the L-lysyl residue with the C-terminal carboxylic acid group. It is the major component of bacitracin. It has a role as an antibacterial agent and an antimicrobial agent. It is a homodetic cyclic peptide and a polypeptide.
Bacitracin, also known as baci-RX or zinc bacitracin, belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Bacitracin is a drug which is used for the treatment of infants with pneumonia and empyema caused by staphylococci shown to be susceptible to the drug. also used in ointment form for topical treatment of a variety of localized skin and eye infections, as well as for the prevention of wound infections. used against gram positive bacteria. bacitracin is also used as an inhibitor of proteases and other enzymes. however, specific activity of bactracin's inhibition of protein disulfide isomerase has been called into question. . Bacitracin exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Bacitracin has been detected in multiple biofluids, such as urine and blood. Within the cell, bacitracin is primarily located in the cytoplasm.
Bacitracin is a combination of at least 9 bacitracins. 60-80% of commercially prepared bacitracin is bacitracin A. The bacillus that produces bacitracin was first isolated from a knee scrape in 1945 from the knee wound of a child named Margaret Tracy. Bacitracin was granted FDA approval on 29 July 1948.
1422.7 g/mol
$ $99 In stock
Formulation: 1422.7 g/mol
Source:
Usage:
Bacitracin A (8CI) - 22601-59-8

Bacitracin A (8CI)

The product is for non-human research only. Not for therapeutic or veterinary use.

Catalog Number: BT-242084

CAS Number: 22601-59-8

Molecular Formula: C66H103N17O16S

Molecular Weight: 1422.7 g/mol

CAS Number 22601-59-8
Product Name Bacitracin A (8CI)
Molecular Formula C66H103N17O16S
Molecular Weight 1422.7 g/mol
InChI InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-72-32-48(100-66)63(97)80-43(26-34(4)5)59(93)75-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)76-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-73-39)77-60(94)44(27-38-18-13-12-14-19-38)81-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)74-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,73)(H,71,89)(H,74,90)(H,75,93)(H,76,98)(H,77,94)(H,78,96)(H,79,95)(H,80,97)(H,81,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35?,36?,37?,40-,41+,42+,43-,44+,45-,46-,47+,48?,52-,53-,54-/m0/s1
InChI Key CLKOFPXJLQSYAH-ABRJDSQDSA-N
Isomeric SMILES CC[C@H](C)[C@@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CSC(=N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
IUPAC Name (4R)-4-[[(2S)-2-[[2-[(1S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-5-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-butan-2-yl-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
Canonical SMILES CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CN=C(S2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
Description Bacitracin A is a homodetic cyclic peptide consisting of (4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid attached head-to-tail to L-leucyl,D-glutamyl, L-lysyl, D-ornityl, L-isoleucyl, D-phenylalanyl, L-histidyl. D-aspartyl and L-asparaginyl residues coupled in sequence and cyclised by condensation of the side-chain amino group of the L-lysyl residue with the C-terminal carboxylic acid group. It is the major component of bacitracin. It has a role as an antibacterial agent and an antimicrobial agent. It is a homodetic cyclic peptide and a polypeptide.
Bacitracin, also known as baci-RX or zinc bacitracin, belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Bacitracin is a drug which is used for the treatment of infants with pneumonia and empyema caused by staphylococci shown to be susceptible to the drug. also used in ointment form for topical treatment of a variety of localized skin and eye infections, as well as for the prevention of wound infections. used against gram positive bacteria. bacitracin is also used as an inhibitor of proteases and other enzymes. however, specific activity of bactracin's inhibition of protein disulfide isomerase has been called into question. . Bacitracin exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Bacitracin has been detected in multiple biofluids, such as urine and blood. Within the cell, bacitracin is primarily located in the cytoplasm.
Bacitracin is a combination of at least 9 bacitracins. 60-80% of commercially prepared bacitracin is bacitracin A. The bacillus that produces bacitracin was first isolated from a knee scrape in 1945 from the knee wound of a child named Margaret Tracy. Bacitracin was granted FDA approval on 29 July 1948.
Melting Point 221-225°C
Other CAS Number 22601-59-8
1405-87-4
Physical Description Solid
Related CAS 1405-89-6 (zinc complex)
SMILES CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CN=C(S2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
Solubility Freely soluble
2.45e-02 g/L
Synonyms bacitracin A
Reference 1: Wan EC, Ho C, Sin DW, Wong YC. Detection of residual bacitracin A, colistin A, and colistin B in milk and animal tissues by liquid chromatography tandem mass spectrometry. Anal Bioanal Chem. 2006 May;385(1):181-8. Epub 2006 Mar 18. PubMed PMID: 16547744.
PubChem Compound Bacitracin A (8CI)
Last Modified Apr 13 2022