The Alkaline Cleavage of Desyl Thioethers

Teich, Sylvia; Curtin, David Y.

doi:10.1021/ja01162a035

Cited by 11 publications

(6 citation statements)

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“…3. Because ahaloketones are considered to react with nucleophilic functional groups such as the SH group, 41,42) and therefore a-haloketones may react with the free SH groups of the enzyme and may thereby inactivate it. Existence of the free SH groups in Pseudomonas FDH has been suggested previously.…”

Section: Resultsmentioning

confidence: 99%

Purification and Characterization of an α-Haloketone-resistant Formate Dehydrogenase fromThiobacillussp. Strain KNK65MA, and Cloning of the Gene

Nanba

Takaoka

Hasegawa

2003

Bioscience, Biotechnology, and Biochemistry

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Thiobacillus sp. strain KNK65MA, which produced an NAD-dependent formate dehydrogenase (FDH) highly resistant to alpha-haloketones, was newly isolated, i.e., the enzyme showed no loss of activity after a 5-h incubation with alpha-haloketones, such as ethyl 4-chloro-3-oxobutanoate. The enzyme was also resistant to SH reagents. The enzyme, purified to homogeneity, was a dimer composed of identical subunits. The specific activity was 7.6 u/mg, and the apparent Km values for formate and NAD+ were 1.6 and 0.048 mM, respectively. The cloned gene of FDH contained one open reading frame (ORF) of 1206 base pairs, predicted to encode a polypeptide of 401 amino acids, with a calculated molecular weight of 44,021; this gene was highly expressed in E. coli cells. The deduced amino acid sequence of this FDH had high identity to other bacterial FDHs.

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Section: Resultsmentioning

confidence: 99%

Purification and Characterization of an α-Haloketone-resistant Formate Dehydrogenase fromThiobacillussp. Strain KNK65MA, and Cloning of the Gene

Nanba

Takaoka

Hasegawa

2003

Bioscience, Biotechnology, and Biochemistry

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“…is 77°.17 ^-Methoxybenzyl phenyl ketone was prepared from 4-methoxybenzoin17 by reduction with thioglycolic acid followed by sodium carbonate. 18 The yield was 37% of product, m.p. 94.5-95°( reported17 96.5°).…”

Section: Experimental12mentioning

confidence: 97%

“…[Contribution from the Department of Chemistry, Purdue University] The Ionization Constants of Some New Fluorine-containing Acidsla Received January 18,1954 The acids CF3CH=CHC02H and C3F7CH=CHC02H are stronger than CF3CH2CH2C02H and C3F7CH2CH2C02H; and considerably stronger than their non-fluorinated analogs, but they are much weaker acids than 0F3CO2H or C3F7C02H.…”

Section: Urbana Illinoismentioning

confidence: 99%

Migration Ratios in the Rearrangement of 2-Amino-1,1-diarylethanols¹

Curtin¹,

Crew²

1954

J. Am. Chem. Soc.

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“…ArCOCHSCH2COOH + NaOH -» ArCOCH2R + I R (HOSCH2COOH) -» H2S + CHOCOOH (IV-37)When R = H, the product is (C6H5COCH2)2CHCOOH, evidently produced by further condensation of the acetophenone formed initially, with the glyoxylic acid. The following alternative mechanism has also been suggested(414the type shown below give carbon-carbon cleavage with alkali, like a /3-keto ester (38, 414): ArCOCHCeHs -^C 6H6COOH + RSCH2C6H6 (IV-39) SR R = C6H4COOH(oor m-), C2H6.…”

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confidence: 99%