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Guanidylfungin B

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Category Antibiotics
Catalog number BBF-01298
CAS 94116-20-8
Molecular Weight 1116.42
Molecular Formula C57H101N3O18

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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 Streptomyces hygroscopicus 662. It is a macrolide antibiotic. It has weak anti-gram-negative bacterial and fungal activity.

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Synonyms Guanidylfungin A, N-demethyl-, (9alpha,11alpha,13E,15S)-
IUPAC Name 3-[[(10Z,20E)-15-[(E)-10-(diaminomethylideneamino)-4-methyldec-4-en-2-yl]-3,5,7,9,23,25,27,31,33,34,35-undecahydroxy-8,10,14,18,22,26,30-heptamethyl-17-oxo-16,37-dioxabicyclo[31.3.1]heptatriaconta-10,20-dien-19-yl]oxy]-3-oxopropanoic acid
Canonical SMILES CC1CCC=C(C(C(C(CC(CC(CC2CC(C(C(O2)(CC(C(CCC(C(C(CC(C(C=CC(C(C(=O)OC1C(C)CC(=CCCCCCN=C(N)N)C)C)OC(=O)CC(=O)O)C)O)O)C)O)C)O)O)O)O)O)O)O)C)O)C
InChI InChI=1S/C57H101N3O18/c1-31(15-12-10-11-13-22-60-56(58)59)23-36(6)53-35(5)17-14-16-34(4)52(72)38(8)45(65)26-41(62)24-40(61)25-42-27-47(67)54(73)57(75,78-42)30-48(68)33(3)18-20-43(63)37(7)46(66)28-44(64)32(2)19-21-49(39(9)55(74)77-53)76-51(71)29-50(69)70/h15-16,19,21,32-33,35-49,52-54,61-68,72-73,75H,10-14,17-18,20,22-30H2,1-9H3,(H,69,70)(H4,58,59,60)/b21-19+,31-15+,34-16-
InChI Key DVNBCGGJVDKDQA-AGGPENHYSA-N
Appearance White Fine Acicular Crystal
Antibiotic Activity Spectrum Gram-negative bacteria; Fungi
Boiling Point 1193.0 °C at 760 mmHg
Melting Point 138-142 °C (dec.)
Density 1.29 g/cm3
Solubility Insoluble in Water
1. Studies on new antifungal antibiotics, guanidylfungins A and B. II. Structure elucidation and biosynthesis
K Takesako, T Beppu J Antibiot (Tokyo). 1984 Oct;37(10):1170-86. doi: 10.7164/antibiotics.37.1170.
The structures of guanidylfungins A and B were elucidated from the physico-chemical properties of these compounds and the structures of the degradation products by ozonolysis and periodate oxidation. The guanidylfungins consist of a 36-membered polyhydroxyl lactone ring, a guanidine and a monoester of malonic acid. The labelling experiments with sodium [1-13C]acetate and sodium [1-13C]propionate revealed that twelve units of acetate and nine of propionate were incorporated into the molecule of guanidylfungin A.
2. Studies on new antifungal antibiotics, guanidylfungins A and B. I. Taxonomy, fermentation, isolation and characterization
K Takesako, T Beppu J Antibiot (Tokyo). 1984 Oct;37(10):1161-9. doi: 10.7164/antibiotics.37.1161.
Guanidylfungin A, C58H103N3O18, and guanidylfungin B, C57H101N3O18, were isolated from the mycelia of Streptomyces hygroscopicus No. 662 by means of silica gel absorption and reversed phase liquid chromatographies. The guanidylfungins were active against fungi and Gram-negative bacteria.
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