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Janthinocin B

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Janthinocin B
Category Antibiotics
Catalog number BBF-01519
CAS 131086-53-8
Molecular Weight 1191.33
Molecular Formula C57H82N12O16

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 1535°C at 760 mmHg
Density 1.38 g/cm3
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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