Katanosin A
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| Category | Antibiotics |
| Catalog number | BBF-01533 |
| CAS | 116103-86-7 |
| Molecular Weight | 1262.45 |
| Molecular Formula | C57H95N15O17 |
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Description
Katanosin A is a peptide antibiotic originally isolated from Cytophaga sp. PBJ-5356. It has anti-gram-positive bacterial effect.
Specification
| Synonyms | L-Serine, N-[threo-3-hydroxy-N2-[N-[N-[N-[N2-[N-[threo-3-hydroxy-N-[threo-b-hydroxy-N-(N-D-leucyl-L-leucyl)-L-phenylalanyl]-L-leucyl]-L-leucyl]-D-arginyl]-L-valyl]-L-allothreonyl]glycyl]-L-asparaginyl]-,b1-lactone |
| IUPAC Name | 2-amino-N-[1-[[6-(2-amino-1-hydroxy-2-oxoethyl)-18-[3-(diaminomethylideneamino)propyl]-12-(1-hydroxyethyl)-3-(hydroxymethyl)-24-(1-hydroxy-2-methylpropyl)-21-(2-methylpropyl)-2,5,8,11,14,17,20,23,26-nonaoxo-28-phenyl-15-propan-2-yl-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]amino]-4-methyl-1-oxopentan-2-yl]-4-methylpentanamide |
| Canonical SMILES | CC(C)CC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)OC(C(C(=O)NC(C(=O)N1)C(C(C)C)O)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)N)C2=CC=CC=C2)CO)C(C(=O)N)O)C(C)O)C(C)C)CCCN=C(N)N |
| InChI | InChI=1S/C57H95N15O17/c1-25(2)20-32(58)47(79)65-35(22-27(5)6)50(82)72-42-45(31-16-13-12-14-17-31)89-56(88)36(24-73)67-54(86)41(44(77)46(59)78)68-37(75)23-63-51(83)39(30(11)74)70-52(84)38(28(7)8)69-48(80)33(18-15-19-62-57(60)61)64-49(81)34(21-26(3)4)66-53(85)40(71-55(42)87)43(76)29(9)10/h12-14,16-17,25-30,32-36,38-45,73-74,76-77H,15,18-24,58H2,1-11H3,(H2,59,78)(H,63,83)(H,64,81)(H,65,79)(H,66,85)(H,67,86)(H,68,75)(H,69,80)(H,70,84)(H,71,87)(H,72,82)(H4,60,61,62) |
| InChI Key | SHQGVBSYOMBSEU-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 240-245°C |
| Density | 1.43 g/cm3 |
Reference Reading
1. The structures of katanosins A and B
T Kato, H Hinoo, Y Terui, J Kikuchi, J Shoji J Antibiot (Tokyo). 1988 Jun;41(6):719-25. doi: 10.7164/antibiotics.41.719.
1H and 13C NMR studies on katanosin A confirmed the presence of eight usual amino acid residues which were previously deduced by amino acid analysis and suggested the presence of beta-hydroxyaspartic acid, beta-hydroxyleucine and beta-phenylserine residues. These amino acids were isolated and confirmed, including their stereochemistries, by comparison with the respective authentic specimens. Stereochemistries of the usual amino acids were determined by comparing the L-leucylated amino acids with reference compounds by HPLC. Lithium borohydride reduction and chromic acid oxidation of katanosin A and alkali-treated katanosin A elucidated a lactone linkage between the C-terminal Ser and phenylserine residues. Edman degradation on alkali-treated katanosin A clarified the total amino acid sequence. The difference in katanosins A and B was determined to be replacement of Val in A by Ile in B. Thus, the structures of katanosins A and B were elucidated.
2. Isolation and characterization of katanosins A and B
J Shoji, H Hinoo, K Matsumoto, T Hattori, T Yoshida, S Matsuura, E Kondo J Antibiot (Tokyo). 1988 Jun;41(6):713-8. doi: 10.7164/antibiotics.41.713.
Two peptide antibiotics katanosins A and B were isolated from the culture broth of a strain related to the genus Cytophaga. These antibiotics are basic peptides soluble in aqueous alcohols. The molecular formulae C57H95N15O17 for A and C58H97N15O17 for B were indicated. The constituent amino acids of katanosin A are suggested to be Thr (1), Ser (1), Val (1), Leu (3), Arg (1) and three unusual amino acids. In katanosin B, the Val residue is replaced by Ile. Katanosins A and B are active against Gram-positive bacteria in vitro and in vivo.
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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 ╳
