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Demycarosylplatenomycin

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Demycarosylplatenomycin
Category Antibiotics
Catalog number BBF-00834
CAS
Molecular Weight 613.73
Molecular Formula C31H51NO11

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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

Demycarosylplatenomycin is an antibiotic produced by Streptomyces platensis subsp. malvinus MCRL 0388. It has weak activity against Gram-positive bacteria.

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Synonyms Demycarosylplatenomycin A1
IUPAC Name [(4R,5S,6S,7R,9R,11E,13E,16R)-6-[(2S,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] ethyl carbonate
Canonical SMILES CCOC(=O)OC1CC(=O)OC(CC=CC=CCC(CC(C(C1OC)OC2C(C(C(C(O2)C)O)N(C)C)O)CC=O)C)C
InChI InChI=1S/C31H51NO11/c1-8-39-31(37)42-23-18-24(34)40-20(3)14-12-10-9-11-13-19(2)17-22(15-16-33)28(29(23)38-7)43-30-27(36)25(32(5)6)26(35)21(4)41-30/h9-12,16,19-23,25-30,35-36H,8,13-15,17-18H2,1-7H3/b11-9+,12-10+/t19-,20-,21-,22+,23-,25+,26-,27-,28+,29+,30+/m1/s1
InChI Key LUVTUWILHOMBIL-FTUNUZJWSA-N
Appearance Colorless Flake Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 113-115°C
1. Studies on the biosynthesis of basic 16-membered macrolide antibiotics, platenomycins. II. Production isolation and structures of 3-O-propionyl-5-O-mycaminosyl platenolides I and II, 9-dehydro demycarosyl platenomycin and demycarosyl platenomycin
T Furumai, M Suzuki J Antibiot (Tokyo). 1975 Oct;28(10):775-82. doi: 10.7164/antibiotics.28.775.
Four basic glycosides have been isolated from the fermentation broth of the blocked mutants of Streptomyces platensis subsp. malvinus MCRL 0388. These compounds isolated and purified by solvent extraction and column chromatography were identified as 3-O-propionyl-5-O-mycaminosyl platenolides I (PPL-I-MC) and II (PP-II-MC), 9-dehydro demycarosyl platenomycin (DDM-PLM) and demycarosyl platenomycin (DM-PLM).
2. Studies on the biosynthesis of basic 16-membered macrolide antibiotics, platenomycins. IV. Biosynthesis of platenomycins
T Furumai, K Takeda, M Suzuki J Antibiot (Tokyo). 1975 Oct;28(10):789-97. doi: 10.7164/antibiotics.28.789.
To elucidate the biosynthetic pathway of platenomycin (PLM), biosynthetic relationships of platenolides I (PL-I) and II (PL-II), 3-O-propionyl-5-O-mycaminosyl platenolides I (PPL-I-MC) and II (PPL-UU-MC), 9-dehydro demycarosyl platenomycin (DDM-PLM) were examined with growing cultures or the washed mycelium of blocked mutants of Streptomyces platensis subsp. malvinus MCRL0388, a platenomycin-producing organism. As a result, it was revealed that PLM was biosynthesized from PL-I via DM-PLM and DA-PLM along the pathways shown in Chart 1. 4''-Isovaleroyl unit of PLM-A and 4''-propionyl unit of PLM-B were respectively derived from L-leucine and L-isoleucine.

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