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16-Methyloxazolomycin

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16-Methyloxazolomycin
Category Antibiotics
Catalog number BBF-01930
CAS
Molecular Weight 669.80
Molecular Formula C36H51N3O9

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Product Description

16-Methyloxazolomycin is an antimicrobial and cytotoxic antibiotic produced by a Streptomyces sp.

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Synonyms 16R-Methyloxazolomycin
IUPAC Name (3R,4Z,6Z,8E)-3-hydroxy-N-[(2E,4E,6R,7R,9S)-6-hydroxy-9-[(1R,4S,7R,8S)-8-hydroxy-1,5,7-trimethyl-3,6-dioxo-2-oxa-5-azaspiro[3.4]octan-8-yl]-9-methoxy-7-methylnona-2,4-dienyl]-2,2,4-trimethyl-10-(1,3-oxazol-5-yl)deca-4,6,8-trienamide
Canonical SMILES CC1C(=O)N(C2(C1(C(CC(C)C(C=CC=CCNC(=O)C(C)(C)C(C(=CC=CC=CCC3=CN=CO3)C)O)O)OC)O)C(OC2=O)C)C
InChI InChI=1S/C36H51N3O9/c1-23(16-12-9-10-13-17-27-21-37-22-47-27)30(41)34(5,6)32(43)38-19-15-11-14-18-28(40)24(2)20-29(46-8)36(45)25(3)31(42)39(7)35(36)26(4)48-33(35)44/h9-16,18,21-22,24-26,28-30,40-41,45H,17,19-20H2,1-8H3,(H,38,43)/b12-9-,13-10+,15-11+,18-14+,23-16-/t24-,25+,26-,28+,29+,30-,35-,36-/m1/s1
InChI Key CTNVFWQLXPTQNQ-YTCINQMCSA-N
Appearance Yellow Powder
Antibiotic Activity Spectrum bacteria
Boiling Point 884.7±65.0°C at 760 mmHg
Density 1.2±0.1 g/cm3
1. Lajollamycin, a nitro-tetraene spiro-beta-lactone-gamma-lactam antibiotic from the marine actinomycete Streptomyces nodosus
Rama Rao Manam, Sy Teisan, Donald J White, Benjamin Nicholson, Jennifer Grodberg, Saskia T C Neuteboom, Kin S Lam, Deborah A Mosca, G Kenneth Lloyd, Barbara C M Potts J Nat Prod. 2005 Feb;68(2):240-3. doi: 10.1021/np049725x.
A strain of Streptomyces nodosus (NPS007994) isolated from a marine sediment collected in Scripps Canyon, La Jolla, California, was found to produce lajollamycin (1), a nitro-tetraene spiro-beta-lactone-gamma-lactam antibiotic. The structure was established by complete analysis of spectroscopic data and comparison with known antibiotics oxazolomycin (2), 16-methyloxazolomycin (3), and triedimycin B (4). Lajollamycin (1) showed antimicrobial activity against both drug-sensitive and -resistant Gram-positive bacteria and inhibited the growth of B16-F10 tumor cells in vitro.
2. Progress in the total synthesis of inthomycins
Bidyut Kumar Senapati Beilstein J Org Chem. 2021 Jan 7;17:58-82. doi: 10.3762/bjoc.17.7. eCollection 2021.
The inthomycin family of antibiotics, isolated from Streptomyces strains, are interesting molecules for synthesis due to their characteristic common oxazole polyene chiral allylic β-hydroxycarbonyl fragments and significant biological activities. The full structural motif of the inthomycins is found in several more complex natural products including the oxazolomycins, 16-methyloxazolomycin, curromycins A and B, and KSM-2690. This review summarises the application of various efforts towards the synthesis of inthomycins and their analogues systematically.
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16-Methyloxazolomycin

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