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86305

Sigma-Aldrich

Tautomycin from Streptomyces spiroverticillatus

≥90% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C41H66O13
CAS Number:
109946-35-2
Molecular Weight:
766.95
Beilstein:
3583132
UNSPSC Code:
12352200
PubChem Substance ID:
329769454
NACRES:
NA.25

biological source

Streptomyces spiroverticillatus

Assay

≥90% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CO[C@@H]([C@H](O)CC(=O)[C@@H](C)[C@@H](O)CC[C@@H](C)C1O[C@]2(CC[C@@H](C)[C@H](CC[C@H](C)C(C)=O)O2)CC[C@@H]1C)[C@H](OC(=O)C[C@@H](O)C3=C(C)C(=O)OC3=O)C(C)C

InChI

1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38-,41+/m0/s1

InChI key

RFCWHQNNCOJYTR-QKIDKDKQSA-N

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Application

Tautomycin from Streptomyces spiroverticillatus may be used to study its potential as an anti-fungal and anticancer agent. Tautomycin may be used as a potent and specific protein phosphatase inhibitor.

Other Notes

Potent and specific inhibitor of protein phosphatases 1 and 2A

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P264 - P301 + P310

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wenli Li et al.
Journal of natural products, 72(3), 450-459 (2009-02-05)
Tautomycetin (TTN) is a highly potent and specific protein phosphatase inhibitor isolated from Streptomyces griseochromogenes. The biological activity of TTN makes it an important lead for drug discovery, whereas its rare dialkylmaleic anhydride moiety and structural similarity to tautomycin (TTM)
Scott N Pinchot et al.
American journal of surgery, 197(3), 313-319 (2009-02-28)
Carcinoids are neuroendocrine (NE) tumors with limited treatment options. Raf-1 pathway activation has been shown to suppress hormone production in carcinoid cells. We investigated a novel treatment for carcinoid cell growth based on pharmacologic Raf-1 activation using the compound tautomycin
Xiaolong Chen et al.
The Journal of antibiotics, 64(8), 563-569 (2011-07-21)
The potential of tautomycin to control oilseed rape stem rot was investigated in this paper. Tautomycin produced by Streptomyces spiroverticillatus strongly inhibited Sclerotinia sclerotiorum, which causes oilseed rape stem rot. Tautomycin showed great inhibition of the mycelial growth of S.
Sijiu Liu et al.
Chemistry & biology, 18(1), 101-110 (2011-02-01)
SHP2 phosphatase is a positive transducer of growth factor and cytokine signaling. SHP2 is also a bona fide oncogene; gain-of-function SHP2 mutations leading to increased phosphatase activity cause Noonan syndrome, as well as multiple forms of leukemia and solid tumors.
Minoru Isobe et al.
Chemistry, an Asian journal, 2(3), 377-385 (2007-04-19)
We have accomplished the synthesis of 13C-labeled tautomycin at the C18, C19, C21, and C22 positions starting from 100% [13C]triethylphosphonoacetate for the purpose of elucidating the dynamics and conformation of the C17-C26 moiety. NMR spectroscopy of 13C-labeled tautomycin revealed strong
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