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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:
Molecular Weight:
766.95
Beilstein/REAXYS Number:
3583132
UNSPSC Code:
12352200
PubChem Substance ID:
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[1]

Pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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C MacKintosh et al.
FEBS letters, 277(1-2), 137-140 (1990-12-17)
Tautomycin inhibited the catalytic subunits of protein phosphatase-1 (Kiapp = 0.16 nM) more potently than protein phosphatase 2A (Kiapp = 0.4 nM), and the native forms of these enzymes in mammalian, protozoan and plant extracts were inhibited in a similar
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.
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
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.
Wenli Li et al.
The Journal of biological chemistry, 283(42), 28607-28617 (2008-08-19)
Tautomycin (TTM) is a highly potent and specific protein phosphatase inhibitor isolated from Streptomyces spiroverticillatus. The biological activity of TTM makes it an important lead for drug discovery, whereas its spiroketal-containing polyketide chain and rare dialkylmaleic anhydride moiety draw attention

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