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A2836

Sigma-Aldrich

Ansamitocin P-3 from Actinosynnema pretiosum

≥90% (HPLC)

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About This Item

Fórmula empírica (notación de Hill):
C32H43ClN2O9
Número de CAS:
66584-72-3
Peso molecular:
635.14
MDL number:
MFCD00274586
UNSPSC Code:
12352202
PubChem Substance ID:
24890696
NACRES:
NA.32

Quality Level

200

assay

≥90% (HPLC)

form

powder

storage temp.

2-8°C

SMILES string

CO[C@@H]1\C=C\C=C(C)\Cc2cc(OC)c(Cl)c(c2)N(C)C(=O)C[C@H](OC(=O)C(C)C)[C@]3(C)O[C@@H]3[C@H](C)[C@@H]4C[C@@]1(O)NC(=O)O4

InChI

1S/C32H43ClN2O9/c1-17(2)29(37)43-25-15-26(36)35(6)21-13-20(14-22(40-7)27(21)33)12-18(3)10-9-11-24(41-8)32(39)16-23(42-30(38)34-32)19(4)28-31(25,5)44-28/h9-11,13-14,17,19,23-25,28,39H,12,15-16H2,1-8H3,(H,34,38)/b11-9+,18-10+/t19-,23+,24-,25+,28-,31+,32+/m1/s1

InChI key

OPQNCARIZFLNLF-KUDLRRJMSA-N

Biochem/physiol Actions

Fungal metabolite with antineoplastic, antimitotic activity. Binds to tubulin and inhibits vinblastine-induced spiral formation.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Guo-Zhu Wei et al.
Natural product research, 24(12), 1146-1150 (2010-06-29)
A new compound of ansamitocin was isolated from the extracts of fermentation medium of mutant strain HGF052 derived from Actinosynnema pretiosum ssp. aurantium ATCC 31565, and identified as N-demethyl-desepoxy-9-methoxy-maytansinol (1) on the basis of extensive spectroscopic methods. Bioassay results showed
Florian Taft et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(3), 880-886 (2011-12-16)
Access of four new tumor specific folic acid/ansamitocin conjugates is reported that relies on a synthetic strategy based on the combination of mutasynthesis and semisynthesis. Two bromo-ansamitocin derivatives were prepared by mutasynthesis or by a modified fermentation protocol, respectively, that
The interplay between mutasynthesis and semisynthesis: generation and evaluation of an ansamitocin library.
Simone Eichner et al.
Angewandte Chemie (International ed. in English), 51(3), 752-757 (2011-12-03)
Cyclization of synthetic seco-proansamitocins to ansamitocin macrolactams by Actinosynnema pretiosum as biocatalyst.
Kirsten Harmrolfs et al.
Chembiochem : a European journal of chemical biology, 11(18), 2517-2520 (2010-11-16)
Yingying Wu et al.
Chembiochem : a European journal of chemical biology, 12(11), 1759-1766 (2011-06-18)
Ansamitocins are potent antitumor agents produced by Actinosynnema pretiosum. As deduced from their structures, an N-methylation on the amide bond is required among the various modifications. The protein encoded by asm10 belongs to the SAM-dependent methyltransferase family. Through gene inactivation
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