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Fusacandin B

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Category Antibiotics
Catalog number BBF-01464
CAS 166407-34-7
Molecular Weight 872.90
Molecular Formula C41H60O20

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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 Fusarium sambucinum. It inhibits (1,3)-β-glucan synthetase and has antifungal properties.

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Synonyms D-Glucitol, O-beta-D-galactopyranosyl-(1-2)-O-beta-D-galactopyranosyl-(1-3)-1,5-anhydro-1-C-(2,4-dihydroxy-6-(hydroxymethyl)phenyl)-, 3-((2E,4E,7S,8E,10E)-7-hydroxy-2,4,8,10-hexadecatetraenoate)
IUPAC Name [(2S,3S,4R,5R,6R)-2-[2,4-dihydroxy-6-(hydroxymethyl)phenyl]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl] (2E,4E,8E,10E)-7-hydroxyhexadeca-2,4,8,10-tetraenoate
Canonical SMILES CCCCCC=CC=CC(CC=CC=CC(=O)OC1C(C(OC(C1OC2C(C(C(C(O2)CO)O)O)OC3C(C(C(C(O3)CO)O)O)O)CO)C4=C(C=C(C=C4O)O)CO)O)O
InChI InChI=1S/C41H60O20/c1-2-3-4-5-6-7-9-12-22(46)13-10-8-11-14-28(49)59-38-35(55)37(29-21(17-42)15-23(47)16-24(29)48)56-27(20-45)36(38)60-41-39(33(53)31(51)26(19-44)58-41)61-40-34(54)32(52)30(50)25(18-43)57-40/h6-12,14-16,22,25-27,30-48,50-55H,2-5,13,17-20H2,1H3/b7-6+,10-8+,12-9+,14-11+/t22?,25-,26-,27-,30+,31+,32+,33+,34-,35+,36-,37+,38-,39-,40+,41+/m1/s1
InChI Key DEPSCDXHCFJSQZ-QICRFORPSA-N
Appearance White Solid
Antibiotic Activity Spectrum fungi
Melting Point 42-45°C
1. Fusacandins A and B; novel antifungal antibiotics of the papulacandin class from Fusarium sambucinum. I. Identity of the producing organism, fermentation and biological activity
M Jackson, D J Frost, J P Karwowski, P E Humphrey, S K Dahod, W S Choi, K Brandt, L H Malmberg, R R Rasmussen, M H Scherr, et al. J Antibiot (Tokyo). 1995 Jul;48(7):608-13. doi: 10.7164/antibiotics.48.608.
The fuscandins, antifungal agents of the papulacandin class, are produced by a strain of Fusarium sambucinum. Fermentation yielded 60 mg/liter of fusacandin A and minor amounts of fusacandin B. As expected, the fusacandins inhibit (1,3)-beta-glucan synthesis. Fusacandin A is slightly less active than papulacandin B against Candida albicans and, like papulacandin, loses activity in the presence of serum.
2. Fusacandins A and B; novel antifungal antibiotics of the papulacandin class from Fusarium sambucinum. II. Isolation and structural elucidation
J E Hochlowski, D N Whittern, A Buko, L Alder, J B McAlpine J Antibiot (Tokyo). 1995 Jul;48(7):614-8. doi: 10.7164/antibiotics.48.614.
Two novel antifungal compounds of the papulacandin class, named fusacandins A and B, have been isolated from Fusarium sambucinum. Each compound contains two units of galactose and one of glucose, the latter connected as a C-glycoside to an aromatic moiety. Fusacandin A is esterified at two sites with long-chain, unsaturated fatty acids and fusacandin B at only one site. The structures of the fusacandins were elucidated through analysis of mass spectral and 1-D and 2-D homonuclear and heteronuclear NMR data.

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