Tubulysin D
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| Category | Antibiotics |
| Catalog number | BBF-02728 |
| CAS | 309935-57-7 |
| Molecular Weight | 828.07 |
| Molecular Formula | C43H65N5O9S |
| Purity | ≥98% |
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Description
Tubulysin D is a tetrapeptide isolated from the myxobacterial species Archangium geophyra and Angiococcus disciformis. It displays potent antitumor activity and leads to cell cycle arrest and apoptosis by inhibiting tubulin polymerization with an IC50 of 1.7 μM. Tubulysin displays extremely potent cytotoxic activity in mammalian cells, including multidrug-resistant cell lines, with IC50 values in the lower nanomolar range.
Specification
| Synonyms | (+)-Tubulysin D |
| IUPAC Name | (2S,4R)-4-[[2-[(1R,3R)-1-acetyloxy-4-methyl-3-[3-methylbutanoyloxymethyl-[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]pentyl]-1,3-thiazole-4-carbonyl]amino]-2-methyl-5-phenylpentanoic acid |
| Canonical SMILES | CCC(C)C(C(=O)N(COC(=O)CC(C)C)C(CC(C1=NC(=CS1)C(=O)NC(CC2=CC=CC=C2)CC(C)C(=O)O)OC(=O)C)C(C)C)NC(=O)C3CCCCN3C |
| InChI | InChI=1S/C43H65N5O9S/c1-10-28(6)38(46-40(52)34-18-14-15-19-47(34)9)42(53)48(25-56-37(50)20-26(2)3)35(27(4)5)23-36(57-30(8)49)41-45-33(24-58-41)39(51)44-32(21-29(7)43(54)55)22-31-16-12-11-13-17-31/h11-13,16-17,24,26-29,32,34-36,38H,10,14-15,18-23,25H2,1-9H3,(H,44,51)(H,46,52)(H,54,55)/t28-,29-,32+,34+,35+,36+,38-/m0/s1 |
| InChI Key | SAJNCFZAPSBQTQ-HZZFHOQESA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 950.5±65.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Total syntheses of tubulysins
Taku Shibue, Toshihiro Hirai, Iwao Okamoto, Nobuyoshi Morita, Hyuma Masu, Isao Azumaya, Osamu Tamura Chemistry. 2010 Oct 11;16(38):11678-88. doi: 10.1002/chem.201000963. Epub 2010 Aug 23.
The total syntheses of tetrapeptides tubulysins D (1 b), U (1 c), and V (1 d), which are potent tubulin polymerization inhibitors, are described. The synthesis of Tuv (2), an unusual amino acid constituent of tubulysins, includes an 1,3-dipolar cycloaddition reaction of chiral nitrone D-6 derived from D-gulose with N-acryloyl camphor sultam (-)-9 employing the double asymmetric induction, whereas the synthesis of Tup (20), another unusual amino acid, involves a stereoselective Evans aldol reaction of (Z)-boron enolate generated from (S)-4-isopropyl-3-propionyl-2-oxazolidinone with N-protected phenylalaninal and a subsequent Barton deoxygenation protocol. We accomplished the total syntheses of tubulysins U (1 c) and V (1 d) by using these methodologies, in which the isoxazolidine ring was used as the effective protective group for γ-amido alcohol functionality. Furthermore, to understand the structure-activity relationship of tubulysins, we synthesized tubulysin D (1 b) and cyclo-tubulysin D (1 e) from 2-Me and 20, and ent-tubulysin D (ent-1 d) from ent-2-Me and ent-20, respectively. The preliminary results regarding their biological activities are also reported.
2. Synthesis and biological evaluation of tubulysin D analogs related to stereoisomers of tubuvaline
Taku Shibue, Iwao Okamoto, Nobuyoshi Morita, Hiroshi Morita, Yusuke Hirasawa, Takahiro Hosoya, Osamu Tamura Bioorg Med Chem Lett. 2011 Jan 1;21(1):431-4. doi: 10.1016/j.bmcl.2010.10.118. Epub 2010 Oct 30.
The synthesis and biological evaluation of stereoisomers in tubulysin D are described. The stereoselective synthesis of all possible stereoisomers of C-11 and C-13 positions in tubulysin D was achieved by employing 1'-epi-Tuv-Me, 3'-epi-Tuv-Me, and ent-Tuv-Me and their biological properties were evaluated. It is clear that the stereochemistries of the C-11 and C-13 positions in tubulysin D have no practical impact on the inhibition of tubulin polymerization but play a role in the potent antiproliferative activities.
3. Toward tubulysin: gram-scale synthesis of tubuvaline-tubuphenylalanine fragment
Srivari Chandrasekhar, Bodugam Mahipal, Mitta Kavitha J Org Chem. 2009 Dec 18;74(24):9531-4. doi: 10.1021/jo9015503.
A practical and stereoselective synthesis of the tubuvaline-tubuphenylalanine (Tuv-Tup) fragment of tubulysin is achieved involving the opening of aziridine, crucial MacMillan alpha-hydroxylation on both fragments, and an epoxide-opening reaction.
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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 ╳
