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Isoapoptolidin

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Isoapoptolidin
Category Enzyme inhibitors
Catalog number BBF-04604
CAS 476647-30-0
Molecular Weight 1129.38
Molecular Formula C58H96O21
Purity >90% by HPLC

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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

It is a ring expanded isomer of apoptolidin originally isolated from Nocardiopsis sp. It demonstrates 10-fold reduced F1FO-ATP synthase inhibitory activity compared to apoptolidin (IC50s = 17 and 0.7 µM, respectively).

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Synonyms (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S,21R)-10-[(6-Deoxy-4-O-methyl-α-L-glucopyranosyl)oxy]-21-[O-2,6-dideoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1→4)-O-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1→7)-2,4,6-trideoxy-1-C-hydroxy-2,4-dimethyl-8-O-methyl-L-glycero-β-D-galacto-octopyranosyl]-17,20-dihydroxy-18-methoxy-3,5,7,9,13-pentamethyloxacycloheneicosa-3,5,7,11,13-pentaen-2-one; Isoapoptolidin A
Storage Store at -20°C
IUPAC Name (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S,21R)-21-[(2R,3R,4S,5R,6R)-2,4-dihydroxy-6-[(2R)-2-[(2R,4S,5S,6S)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethyloxan-2-yl]oxy-3-methoxypropyl]-3,5-dimethyloxan-2-yl]-10-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17,20-dihydroxy-18-methoxy-3,5,7,9,13-pentamethyl-1-oxacyclohenicosa-3,5,7,11,13-pentaen-2-one
Canonical SMILES CC1C=C(C=C(C=C(C(=O)OC(C(CC(C(CCC=C(C=CC1OC2C(C(C(C(O2)C)OC)O)O)C)O)OC)O)C3(C(C(C(C(O3)CC(COC)OC4CC(C(C(O4)C)OC5CC(C(C(O5)C)O)OC)(C)O)C)O)C)O)C)C)C
InChI InChI=1S/C58H96O21/c1-29-17-16-18-40(59)44(69-13)25-41(60)54(78-55(65)33(5)23-31(3)21-30(2)22-32(4)42(20-19-29)76-56-51(64)50(63)52(71-15)37(9)74-56)58(67)35(7)48(61)34(6)43(79-58)24-39(28-68-12)75-47-27-57(11,66)53(38(10)73-47)77-46-26-45(70-14)49(62)36(8)72-46/h17,19-23,32,34-54,56,59-64,66-67H,16,18,24-28H2,1-15H3/b20-19+,29-17+,30-22+,31-21+,33-23+/t32-,34+,35-,36-,37+,38+,39-,40+,41+,42-,43-,44+,45-,46+,47+,48+,49-,50+,51+,52+,53+,54-,56+,57+,58-/m1/s1
InChI Key BGIXVQPJBLGABA-PVLPSINKSA-N
Source Amycolatopsis sp.
Appearance White Solid
Boiling Point 1109.3±65.0°C at 760 mmHg
Density 1.3±0.1 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water
1.Isoapoptolidin: structure and activity of the ring-expanded isomer of apoptolidin.
Wender PA1, Gulledge AV, Jankowski OD, Seto H. Org Lett. 2002 Oct 31;4(22):3819-22.
[formula: see text] Apoptolidin (1) is a novel oncolytic lead that induces apoptosis in transformed cell lines with exceptional selectivity. We report the isolation and characterization of a ring-expanded macrolide isomer of apoptolidin: isoapoptolidin (2). The solution conformation of isoapoptolidin is described. The rate of isomerization was measured under biologically relevant conditions and found to approach equilibrium within the time frame of most cell-based assays. Isoapoptolidin's ability to inhibit mitochondrial F0F1-ATPase is over 10-fold less than that of apoptolidin.
2.Toward a stable apoptolidin derivative: identification of isoapoptolidin and selective deglycosylation of apoptolidin.
Pennington JD1, Williams HJ, Salomon AR, Sulikowski GA. Org Lett. 2002 Oct 31;4(22):3823-5.
[formula: see text] Isoapoptolidin was isolated from crude fermentation extracts of the apoptolidin-producing microorganism Nocardiopsis sp. Apoptolidin isomerizes to isoapoptolidin upon treatment with methanolic triethylamine to establish a 1.4:1 equilibrium mixture of isoapoptolidin and apoptolidin. Semisynthesis of a peracetylated and deglycosylated derivative of apoptolidin is also described.

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