Janthinocin B
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| Category | Antibiotics |
| Catalog number | BBF-01519 |
| CAS | 131086-53-8 |
| Molecular Weight | 1191.33 |
| Molecular Formula | C57H82N12O16 |
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Description
It is produced by the strain of Janthinobacterium lividum. Janthinocin B has strong activity of anti-gram-positive bacteria and moderate anti-gram-negative bacteria, and has strong inhibitory effect on drug-resistant staphylococcus such as penicillin, tetracycline, erythromycin, methicillin and gentamicin.
Specification
| Synonyms | 8-(alpha,beta-Didehydro-beta-hydroxytryptophan)janthinocin A; Janthinocin A, 8-(alpha,beta-didehydro-beta-hydroxytryptophan)- |
| IUPAC Name | 2-amino-N-[(9E,15Z)-6-(3-aminopropyl)-3-benzyl-15-ethylidene-24-(1-hydroxyethyl)-9-[hydroxy(1H-indol-3-yl)methylidene]-12,21-bis(hydroxymethyl)-18-(1-hydroxy-2-methylpropyl)-2,5,8,11,14,17,20,23,26-nonaoxo-28-propan-2-yl-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-27-yl]-3-methylpentanamide |
| Canonical SMILES | CCC(C)C(C(=O)NC1C(OC(=O)C(NC(=O)C(NC(=O)C(=C(C2=CNC3=CC=CC=C32)O)NC(=O)C(NC(=O)C(=CC)NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)C(C)O)CO)C(C(C)C)O)CO)CCCN)CC4=CC=CC=C4)C(C)C)N |
| InChI | InChI=1S/C57H82N12O16/c1-9-29(7)40(59)52(79)69-44-47(28(5)6)85-57(84)37(23-31-17-12-11-13-18-31)63-49(76)36(21-16-22-58)62-55(82)43(46(74)33-24-60-35-20-15-14-19-32(33)35)68-50(77)38(25-70)64-48(75)34(10-2)61-54(81)42(45(73)27(3)4)67-51(78)39(26-71)65-53(80)41(30(8)72)66-56(44)83/h10-15,17-20,24,27-30,36-42,44-45,47,60,70-74H,9,16,21-23,25-26,58-59H2,1-8H3,(H,61,81)(H,62,82)(H,63,76)(H,64,75)(H,65,80)(H,66,83)(H,67,78)(H,68,77)(H,69,79)/b34-10-,46-43+ |
| InChI Key | MDODWZNDNCDVHR-YWACARBRSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 1535°C at 760 mmHg |
| Density | 1.38 g/cm3 |
Reference Reading
1. Janthinocins A, B and C, novel peptide lactone antibiotics produced by Janthinobacterium lividum. I. Taxonomy, fermentation, isolation, physico-chemical and biological characterization
J O'Sullivan, J McCullough, J H Johnson, D P Bonner, J C Clark, L Dean, W H Trejo J Antibiot (Tokyo). 1990 Aug;43(8):913-9. doi: 10.7164/antibiotics.43.913.
Janthinocins A, B and C are novel antibacterial agents produced by Janthinobacterium lividum. They were isolated from fermentation broths and characterized by UV, IR, NMR and mass spectroscopy. They are cyclic decapeptide lactones with marked activity against aerobic and anaerobic Gram-positive bacteria and are 2 to 4 times more potent in vitro than vancomycin. Janthinocins A and B were also found to be effective in a Staphylococcus aureus systemic infection in mice.
2. Janthinocins A, B and C, novel peptide lactone antibiotics produced by Janthinobacterium lividum. II. Structure elucidation
J H Johnson, A A Tymiak, M S Bolgar J Antibiot (Tokyo). 1990 Aug;43(8):920-30. doi: 10.7164/antibiotics.43.920.
The structures of janthinocins A, B and C, three novel macrocyclic peptide lactone antibiotics isolated from fermentations of Janthinobacterium lividum, were determined. The janthinocins are of particular interest because they contain three amino acid residues that have not previously been reported in natural products: Each contains erythro-beta-hydroxy-D-leucine while janthinocins A and B also contain beta-hydroxytryptophan and beta-ketotryptophan, respectively.
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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 ╳
