Bacitracin A


CAS No. : 22601-59-8

Bacitracin A,22601-59-8
Product Details
Cat No:P000026
Molecular Formula:C66H103N17O16S
Molecular Weight:1422.713
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Appearance:White to Off-White Solid
Purity:95%(HPLC)
Cat No:P000026
Cas No:22601-59-8
Product-Name:Bacitracin A
IUPAC Name:(4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-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
InChI:InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(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,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(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
InChIKey:CLKOFPXJLQSYAH-ABRJDSQDSA-N
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)C2CSC(=N2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
Bacitracin A(cas 22601-59-8) is the major analogue of the bacitracin complex of cyclic peptides, active against Gram-positive bacteria. Although first reported in 1945, the structure of the bacitracins was not fully elucidated until 1995. Bacitracins form a complex with C55- isoprenyl pyrophosphate and a metal ion to inhibit dephosphorylation and the transport of polysaccharides, peptidoglycans and lipopolysaccharides to the growing cell wall. Bacitracin is used clinically as a topical treatment for skin infections.
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.
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.
2: Lee J, Griffin JH, Nicas TI. Solid-Phase Total Synthesis of Bacitracin A. J Org Chem. 1996 Jun 14;61(12):3983-3986. PubMed PMID: 11667271.
3: Pfeffer-Hennig S, Dauter Z, Hennig M, Höhne W, Wilson K, Betzel C. Three dimensional structure of the antibiotic bacitracin A complexed to two different subtilisin proteases: novel mode of enzyme inhibition. Adv Exp Med Biol. 1996;379:29-41. PubMed PMID: 8796308.
4: Siegel MM, Huang J, Lin B, Tsao R, Edmonds CG. Structures of bacitracin A and isolated congeners: sequencing of cyclic peptides with blocked linear side chains by electrospray ionization mass spectrometry. Biol Mass Spectrom. 1994 Apr;23(4):186-204. PubMed PMID: 8172927.
5: Kobayashi N, Takenouchi T, Endo S, Munekata E. 1H NMR study on the conformation of bacitracin A in aqueous solution. FEBS Lett. 1992 Jun 29;305(2):105-9. PubMed PMID: 1618337.
6: Pons M, Feliz M, Antònia Molins M, Giralt E. Conformational analysis of bacitracin A, a naturally occurring lariat. Biopolymers. 1991 May;31(6):605-12. PubMed PMID: 1932561.
7: Scogin DA, Baldwin TO, Gennis RB. Studies on the complex formed between bacitracin A and divalent cations. Biochim Biophys Acta. 1983 Jan 12;742(1):184-8. PubMed PMID: 6824680.
8: LOCKHART IM, NEWTON GG, ABRAHAM EP. Structure of bacitracin A. Nature. 1954 Mar 20;173(4403):536-7. PubMed PMID: 13154372.
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