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Merck
CN

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

Key Documents

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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

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCBR9881V
BCBM1547V
BCBG8049V
BCBD6614V
BCBD1437

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Magne O Sydnes et al.
Bioorganic & medicinal chemistry, 16(4), 1747-1755 (2007-12-07)
Herein we describe the further improvement of our in-house developed firefly bioluminescence assay system for the determination of inhibition of protein phosphatase (PP). The advantage with the new system is higher sensitivity as well as being time and sample efficient.
Magne O Sydnes et al.
Chemistry, an Asian journal, 5(3), 410-420 (2009-12-17)
It has been a long journey since tautomycin (TTM) was isolated in 1987 and the discovery that it inhibited protein phosphatase 1 (PP1) more strongly than PP2A until finally the cocrystal structure of TTM and PP1 was presented early in
Jianhua Ju et al.
Organic letters, 11(7), 1639-1642 (2009-03-14)
The biosynthetic gene cluster for tautomycin (TTM), a potent protein phosphatase (PP) inhibitor has recently been characterized. Inactivation of ttmM, which encodes a putative C3' hydroxylase, afforded mutant SB6005 which accumulated three new 3'-deshydroxy TTM analogs, supporting the function of
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
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)
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