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Nanaomycin C

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Category Antibiotics
Catalog number BBF-01982
CAS 58286-55-8
Molecular Weight 301.29
Molecular Formula C16H15NO5

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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

Nanaomycin C is an antibiotic produced by Str. rosa subsp. notoensis. It has anti-gram-positive bacteria, mycobacteria, mycoplasma and a few fungi activity.

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Synonyms 1H-Naphtho(2,3-c)pyran-3-acetamide, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1S-trans)-
Storage Store at -20°C
IUPAC Name 2-[(1R,3S)-9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetamide
Canonical SMILES CC1C2=C(CC(O1)CC(=O)N)C(=O)C3=C(C2=O)C(=CC=C3)O
InChI InChI=1S/C16H15NO5/c1-7-13-10(5-8(22-7)6-12(17)19)15(20)9-3-2-4-11(18)14(9)16(13)21/h2-4,7-8,18H,5-6H2,1H3,(H2,17,19)/t7-,8+/m1/s1
InChI Key VENLWOFOMJQPFA-SFYZADRCSA-N
Appearance Orange Needle Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; mycoplasma; mycobacteria
Boiling Point 636.6±55.0°C at 760 mmHg
Melting Point 222-224°C (dec.)
Density 1.4±0.1 g/cm3
Solubility Soluble in Methanol, Chloroform
1. Nanaomycins, new antibiotics produced by a strain of Streptomyces. III. A new component, nanaomycin C, and biological activities of nanaomycin derivatives
H Tanaka, H Marumo, T Nagai, M Okada, K Taniguchi J Antibiot (Tokyo). 1975 Dec;28(12):925-30. doi: 10.7164/antibiotics.28.925.
A new component, nanaomycin C, has been isolated from culture medium of Streptomyces rosa var. notoensis, which had been found to produce nanaomycins A and B. Nanaomycin C is an amide of nanaomycin A. Biological activities of nanaomycin C and several derivatives of nanaomycin A are also shown. Acetylnanaomycin A exhibits as strong activities against Gram-positive bacteria, fungi and Mycoplasma gallisepticum as nanaomycin A.
2. Bioconversion and biosynthesis of nanaomycins using cerulenin, a specific inhibitor of fatty acid and polyketide biosyntheses
C Kitao, H Tanaka, S Minami, S Omura J Antibiot (Tokyo). 1980 Jul;33(7):711-6. doi: 10.7164/antibiotics.33.711.
The biosynthetic relationship of the nanaomycins produced by Streptomyces rosa var. notoensis OS-3966 was studied by means of a bioconversion method using the antibiotic cerulenin, a specific inhibitor of fatty acid and polyketide biosyntheses. Nanaomycin D was considered to be the first component produced from the hypothetical intermediate "polyketide". It is proposed that the biosynthesis sequence for the nanaomycin is: nanaomycin D leads to nanaomycin A leads to nanaomycin E leads to nanaomycin B. Nanaomycin B can be converted to nanaomycin A by non-enzymatic dehydration; however, nanaomycin A is rapidly bioconverted to nanaomycin E, which is the major component synthesized by the nanaomycin-producing strain.

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