Actinotetraose Hexatiglate
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| 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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Description
A unique tetrasaccharide with six tiglate esters isolated from an unidentified amycolatopsis culture. It is a potent antitumour agent.
Specification
| 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. |
Properties
| 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 |
Reference Reading
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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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
