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Actinotetraose Hexatiglate

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Actinotetraose Hexatiglate
Category Antibiotics
Catalog number BBF-04592
CAS 216590-44-2
Molecular Weight 1159.18
Molecular Formula C54H78O27
Purity >95% by HPLC

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Capabilities & Facilities

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

A unique tetrasaccharide with six tiglate esters isolated from an unidentified amycolatopsis culture. It is a potent antitumour agent.

  • Specification
  • Properties
  • Reference Reading
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Synonyms Tigloside; 2-[(2E)-2-Methyl-2-butenoate]-O-3,4-bis-O-[(2E)-2-methyl-1-oxo-2-buten-1-yl]-β-D-glucopyranosyl-(1→2)-6-O-[(2E)-2-methyl-1-oxo-2-buten-1-yl]-α-D-glucopyranosyl O-3,4-bis-O-[(2E)-2-methyl-1-oxo-2-buten-1-yl]-β-D-glucopyranosyl-(1→2)-α-D-Glucopyranoside; 2-O-[3,4-bis-O-[(2E)-2-methyl-1-oxo-2-butenyl]-β-D-glucopyranosyl]-6-O-[(2E)-2-methyl-1-oxo-2-butenyl]-α-D-glucopyranosyl 2-O-[3,4-bis-O-[(2E)-2-Methyl-1-oxo-2-butenyl]-β-D-glucopyranosyl]-α-D-Glucopyranoside 6-[(2E)-2-Methyl-2-butenoate]
Storage Store at -20°C
IUPAC Name [(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis[[(E)-2-methylbut-2-enoyl]oxy]oxan-2-yl]oxy-6-[[(E)-2-methylbut-2-enoyl]oxymethyl]oxan-2-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis[[(E)-2-methylbut-2-enoyl]oxy]oxan-2-yl]oxyoxan-2-yl]methyl (E)-2-methylbut-2-enoate
Canonical SMILES CC=C(C)C(=O)OCC1C(C(C(C(O1)OC2C(C(C(C(O2)COC(=O)C(=CC)C)O)O)OC3C(C(C(C(O3)CO)OC(=O)C(=CC)C)OC(=O)C(=CC)C)O)OC4C(C(C(C(O4)CO)OC(=O)C(=CC)C)OC(=O)C(=CC)C)O)O)O
InChI InChI=1S/C54H78O27/c1-13-23(7)45(63)69-21-31-33(57)35(59)43(79-51-37(61)41(77-49(67)27(11)17-5)39(29(19-55)71-51)75-47(65)25(9)15-3)53(73-31)81-54-44(36(60)34(58)32(74-54)22-70-46(64)24(8)14-2)80-52-38(62)42(78-50(68)28(12)18-6)40(30(20-56)72-52)76-48(66)26(10)16-4/h13-18,29-44,51-62H,19-22H2,1-12H3/b23-13+,24-14+,25-15+,26-16+,27-17+,28-18+/t29-,30-,31-,32-,33-,34-,35+,36+,37-,38-,39-,40-,41-,42-,43-,44-,51+,52+,53-,54-/m1/s1
InChI Key BHAUYHDLIURVPC-ZNKXWPPQSA-N
Source Amycolatopsis sp.
Appearance White Powder
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 1118.0±65.0°C at 760 mmHg
Density 1.4±0.1 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO
1. Structure of actinotetraose hexatiglate, a unique glucotetraose from an actinomycete bacterium
E Lacey, R W Rickards, J M Rothschild J Antibiot (Tokyo) . 1998 Dec;51(12):1093-8. doi: 10.7164/antibiotics.51.1093.
An Actinomycete strain A499 belonging to the genera Amycolatopsis or Amycolata isolated from a Western Australian soil sample produced the cyclic decapeptide antibiotic quinaldopeptin (1), together with the actinotetraose hexatiglate (2), the hexa-ester of a novel non-reducing glucotetraose.
2. Actinotetraoses I-K: tetrasaccharide metabolites produced by an insect-derived actinobacteria, Amycolatopsis sp. HCa1
Hui-Ming Ge, Hao-Fu Dai, Rui-Hua Jiao, Ren-Xiang Tan, Zhi-Kai Guo, Wen-Li Mei Chem Biodivers . 2013 Feb;10(2):296-302. doi: 10.1002/cbdv.201200224.
An isolate of rare actinobacteria strain Amycolatopsis sp. HCa1 obtained from the gut of grasshopper produced seven different metabolites in vitro. The metabolites isolated from its mycelia cakes were characterized by NMR and MS analyses. Actinotetraose hexatiglate (or tigloside; 1) with nonreducing glucotetraose skeleton was isolated as a major constituent; three new tetrasaccharide derivatives actinotetraoses I-K (2-4, resp.) and three known actinotetraoses A-C (5-7, resp.) were also isolated.
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