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E0761

Sigma-Aldrich

Ebelactone A microbial

esterase inhibitor

Synonym(s):

3,11-Dihydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-6-tetradecenoic acid 1,3-lactone

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About This Item

Empirical Formula (Hill Notation):
C20H34O4
CAS Number:
76808-16-7
Molecular Weight:
338.48
MDL number:
MFCD00036710
UNSPSC Code:
12352202
PubChem Substance ID:
24894373
NACRES:
NA.77

biological source

Streptomyces sp.

Quality Level

100

assay

≥98% (HPLC)

form

powder

solubility

methanol: 10 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

[H][C@@]1([C@H](C/C(C)=C/[C@H](C([C@H]([C@@H]([C@@H](CC)C)O)C)=O)C)C)OC([C@H]1C)=O

InChI

1S/C20H34O4/c1-8-12(3)17(21)15(6)18(22)13(4)9-11(2)10-14(5)19-16(7)20(23)24-19/h9,12-17,19,21H,8,10H2,1-7H3/b11-9+/t12-,13-,14+,15+,16+,17-,19+/m1/s1

InChI key

WOISDAHQBUYEAF-QIQXJRRPSA-N

General description

Esterase inhibitors produced by Streptomyces sp. MG7-G1 strain

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Amit K Mandal
Organic letters, 4(12), 2043-2045 (2002-06-07)
[structure: see text] The highly stereocontrolled hydroboration of an alkene, a subsequent Suzuki-Miyaura cross-coupling reaction, a silylcupration on a nonterminal acetylene, and an iododesilylation were the key steps in a convergent total synthesis of (-)-ebelactone A.
Low-molecular-weight immunomodifiers produced by micro-organisms.
H Umezawa
Biotechnology & genetic engineering reviews, 3, 255-273 (1985-01-01)
A Scaloni et al.
The Journal of biological chemistry, 269(21), 15076-15084 (1994-05-27)
The presence of a cysteine residue(s) near the active site of acylpeptide hydrolase was suggested by inactivation of the enzyme with sulfhydryl-modifying agents and by the substantial protection against inactivation afforded by the competitive inhibitor acetylmethionine. 5,5'-dithiobis-(2-nitrobenzoate) titrations of the
R Senthilkumar et al.
Experimental eye research, 72(3), 301-310 (2001-02-22)
Acylpeptide hydrolase removes the N -acetylated amino acids from the peptide substrates but not from intact proteins. Cleavage between amino acid residues 203--204 of the native acylpeptide hydrolase results in the formation of a 55 kDa truncated active enzyme in
Gianfranco De Pascale et al.
The Journal of antibiotics, 64(7), 483-487 (2011-04-28)
Homoserine transacetylase (HTA) catalyzes the transfer of an acetyl group from acetyl-CoA to the hydroxyl group of homoserine. This is the first committed step in the biosynthesis of methionine (Met) from aspartic acid in many fungi, Gram-positive and some Gram-negative
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