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InChI=1S/C49H85NO14/c1-11-34(51)26-35-19-17-24-48(62-35)28-37-30(2)38(63-48)29-49(58)33(27-45(5,6)64-49)18-15-13-12-14-16-23-46(7,56)44(55)42(61-40-21-20-36(50(9)10)32(4)59-40)41(53)31(3)43(54)47(8,57)25-22-39(52)60-37/h15,18,22,25,30-38,40-44,51,53-58H,11-14,16-17,19-21,23-24,26-29H2,1-10H3/b18-15+,25-22+/t30-,31+,32?,33+,34+,35+,36?,37-,38-,40?,41+,42-,43-,44+,46+,47+,48+,49-/m0/s1
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Polyketides members in this family have very similar skeleton which means they share a common pathway for their biosynthesis. However, ossamycin modular PKS is rare and unique since its programmed iteration is required to assemble its product considering that only 14 extension modules have to
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accomplish 15 cycles of polyketide chain extension in ossamycin. And cytochrome P450 enzymes are involved in post-PKS oxidation of the ossamycin macrocycle. Unusual 2,3,4,6-deoxyaminohexose sugar L-ossamine need to be attached to C-8 of the ossamycin macrocycle in tailoring stage.
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which is featured with a 6,6-spiroacetal (1,7-dioxaspiro-undecanyl) moiety connected to one side of the macrocycle. Widely-studied 26-membered oligomycins/rutamycins, 24-membered dunaimycins, and 22-membered cytovaricin are also in this family.
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polyketide and a potent inhibitor of the F0 component of mitochondrial F1F0-ATPase, which were shown to be among the top 0.1% most cell line selective cytotoxic agents of 37,000 molecules tested against the 60 human cancer cell lines of the
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Hochlowski JE, Mullaly MM, Brill GM, Whittern DN, Buko AM, Hill P, et al. Dunaimycins, a new complex of spiroketal 24-membered macrolides with immunosuppressive activity. II. Isolation and elucidation of structures. J. Antibiot. 1991;
24:
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Arthur R. Salomon, David W. Voehringer, Leonard A. Herzenberg, and
Chaitan Khosla.Understanding and exploiting the mechanistic basis for selectivity of polyketide inhibitors of F0F1-ATPase. PNAS. 2000; 97(26),
399:. Studies in 1969 showed that ossamycin contained an unusual aminodeoxysaccharide that was given the name, ossamine. After nearly 30 years in 1995, its three-dimensional structure and relative
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Kobayashi K, Nishino C, Ohya J, Sato S, Shiobara Y, Nishimoto N. Oligomycin E, a new antitumor antibiotic produced by
Streptomyces sp. MCI-2225. J. Antibiot. 1987; 40:1053–1057.
40:(1S,3S,6'R,7S,8E,15R,16R,17S,18R,19R,20S,21R,22E,26S,28R,30R)-17-oxy-3,15,16,18,20,21-hexahydroxy-6'--5,5,15,19,21,30-hexamethylspirotriaconta-8,22-diene-28,2'-oxane]-24-one
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Oksana Bilyk, Markiyan
Samborskyy, Peter F. Leadlay.The biosynthetic pathway to ossamycin, a macrocyclic polyketide bearing a spiroacetal moiety. PLoS ONE. 2019.14(4).
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Oksana Bilyk, Markiyan
Samborskyy, Peter F. Leadlay.The biosynthetic pathway to ossamycin, a macrocyclic polyketide bearing a spiroacetal moiety. PLoS ONE. 2019.14(4).
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Herbert A. Kirst, Jon S. Mynderse, James W. Martin, et al. Structure of the
Spiroketal-macrolide Ossamycin. The Journal of Antibiotics. 1996; 94(2), 162-167.
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Kihara T, Kusakabe H, Nakamura G, Sakurai T, Isono K. Cytovaricin, a novel antibiotic. J. Antibiot. 1981; 34:1073–1074.
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CC(C1CCC2(O1)C3((O2)C4((CC(O4)(C)C)/C=C/CCCCC(((((((/C=C/C(=O)O3)(C)O)O)C)O)OC5CCC(C(O5)C)N(C)C)O)(C)O)O)C)O
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354:-derived natural product belonging to a family of 22- to 26-membered
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Except where otherwise noted, data are given for materials in their
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Ossamycin was originally isolated in 1965 from culture broths of
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397:Streptomyces hygroscopicus var. ossamyceticus
372:Streptomyces hygroscopicus var. ossamyceticus
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247:Key: XGECDDPXIKFBTE-ZVNFYDRVSA-N
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405:single crystal X-ray diffraction
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183:RTECS number
46:Identifiers
359:polyketides
356:macrocyclic
277:Properties
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434:References
376:antifungal
315:Molar mass
138:ChemSpider
74:3D model (
63:11015-84-2
53:CAS Number
37:IUPAC name
17:Ossamycin
407:studies.
380:cytotoxic
348:Ossamycin
190:RN1350000
513:Category
391:History
320:912.212
172:5351598
159:PubChem
147:8923652
374:is an
261:SMILES
118:ChEMBL
31:Names
350:is a
236:InChI
98:ChEBI
76:JSmol
378:and
205:EPA
162:CID
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305:O
302:N
296:H
290:C
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