Monitored aminolysis of 3-acylthiazolidine-2-thione : A new convenient synthesis of amide

Nagao, Yoshimitsu; Seno, Kaoru; Kawabata, Kazushige; Miyasaka, T.; Takao, Sachiko; Fujita, Eiichi

doi:10.1016/s0040-4039(00)71520-6

Cited by 79 publications

(27 citation statements)

References 11 publications

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“…When using carboxylic acids activated as the N-hydroxysuccinimide ester and DBU as the base, 23 fairly good results could be obtained. The best results, however, were generated by performing a transamidation reaction, using thiazolidinethiones as the activated form of the chosen acids 24 in the presence of DBU. To our knowledge this reagent has never been used before for the acylation of sulfamates.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Analogues of (E)-1-Hydroxy-2-methylbut-2-enyl 4-Diphosphate, an Isoprenoid Precursor and Human γδ T Cell Activator

et al. 2008

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Abstract:(E)-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate (HMBPP) is an intermediate in the nonmevalonate pathway for the biosynthesis of isoprenoids and also serves as a very strong activator of human  T cells expressing V9/V2 receptors. This paper describes the synthesis of analogues of HMBPP, in which the diphosphate group is replaced by potential isosteric moieties, i.e. carbamate, N-acyl-N'-oxy sulfamate or aminosulfonyl carbamate functionalities. The potential of the synthesized analogues to stimulate V9/V2 T cell response or to inhibit GcpE and LytB, the last enzymes in the non-mevalonate pathway was assessed.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Analogues of (E)-1-Hydroxy-2-methylbut-2-enyl 4-Diphosphate, an Isoprenoid Precursor and Human γδ T Cell Activator

et al. 2008

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“…3-Acyl-2-thiazolidinethione has been reported to acylate amino groups chemoselectively and give amides in good yields [21,221; therefore, only the amino groups on the enzyme are the candidates for the attachment point of PEG-NAD.…”

Section: Discussionmentioning

confidence: 99%

Covalent linking of poly(ethyleneglycol)‐bound NAD with Thermus thermophilus malate dehydrogenase

Eguchi

Iizuka

Kagotani

et al. 1986

European Journal of Biochemistry

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Poly(ethyleneglyco1)-bound NAD (PEG-NAD) was covalently linked to Thermus thermophilus malate dehydrogendse with a bifunctional reagent, 3,3'-(1,6-dioxo-1,6-hexanediyl)bis-2-thiazolidinethione. The covalently linked malate-dehydrogenase -PEG -NAD complex (MDH-PEG-NAD) was purified by DEAE-Sephadex column chromatography to remove unbound PEG-NAD, and fractionated by blue-Sepharose column chromatography into four preparations: MDH-PEG-NAD I, MDH-PEG-NAD 11, MDH-PEG-NAD 111 and MDH-PEG-NAD IV. The average numbers of NAD moieties covalently bound per subunit of MDH-PEG-NAD I, MDH-PEG-NAD 11, MDH-PEG-NAD I11 and MDH-PEG-NAD IV were 1.2, 1.2, 0.8 and 0.5, respectively, and the values were confirmed by sodium dodecyl sulfate/polydcrylamide gel electrophoresis. 60 -80% bound NAD moiety of these preparations of MDH-PEG-NAD was reduced by the enzyme moiety in the presence of Lmalate, and the specific activity of the enzyme moiety of the preparations was more than 80% that of the native enzyme.MDH-PEG-NAD I has the following properties. The K , value for exogeneous NAD is three times that of the native enzyme. The coenzyme activity of its NAD moiety is 20-40% that of native NAD for alcohol and lactate dehydrogenases. The complex catalyzes the oxidation of L-malate in the presence of the redox system of 5-ethylphenazinium ethyl sulfate and a tetrazolium salt with a rate constant of 0.11 s-l. The coenzyme moiety of the complex can also be recycled by coupled reactions of the active site of the same complex and alcohol dehydrogenase. These results indicate that MDH-PEG-NAD works as an NAD(H)-regeneration unit for coupled reactions.A covalently linked dehydrogenase-NAD complex is an attractive catalytic unit if the bound NAD can be used by other enzymes as well as by itself. Such a complex serves as an NAD(H)-regeneration unit in enzyme reactors and also provides many interesting questions about the effects of fixing a readily dissociable coenzyme in the vicinity of an enzyme. Several efforts have been made for this purpose [l -31 but only the alcohol-dehydrogenase -NAD complex, reported by MAnsson et al. [2], has been clearly demonstrated to have covalently bound NAD. As for the complex, recycling of the bound NAD by lactate or malate dehydrogenase [4] and kinetic properties of the alcohol dehydrogenase activity of the complex [5] have also been investigated.We have prepared poly(ethyleneglyco1)-bound NAD (PEG-NAD) as a macromolecular NAD derivative for enzyme reactors [6, 71. PEG-NAD has a unique structure in that one NAD molecule and one amino group are linked with Correspondence to I. Urabe,

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“…[21] Indeed, the thiazolidine-2-thione is a passable leaving group, which sufficiently activates the carboxyl for a reaction with better nucleophiles, even in the dark. In such a case, the nature of the acyl group has little influence on the efficiency of the process; on the other hand, the reaction rate is strongly influenced by the nucleophilicity and the steric bulk of the amine.…”

Section: N-acylthiazolidine-2-thione Derivativesmentioning

confidence: 99%

Photoinduced acyl transfer

Débieux

Bochet

2010

J of Physical Organic Chem

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The acylation reaction occupies a central role in biochemistry and organic synthesis. On the one hand, it is by this very reaction that amino acids successively assemble to form peptides and proteins, and on the other hand it is a major synthetic method encompassing esterification, amidation, Friedel-Crafts reaction and many other processes routinely used both at the laboratory and the industrial scale. Photochemical activation is always an attractive alternative, because it is relatively mild (provided innocuous wavelengths are used), and no additional substance is added; thus no separation of the activator is necessary at the end of the process. In this paper, we briefly survey the most widely used methods of photoinduced acylations, and our own contribution to the field.

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Monitored aminolysis of 3-acylthiazolidine-2-thione : A new convenient synthesis of amide

Cited by 79 publications

References 11 publications

Synthesis of Analogues of (E)-1-Hydroxy-2-methylbut-2-enyl 4-Diphosphate, an Isoprenoid Precursor and Human γδ T Cell Activator

Synthesis of Analogues of (E)-1-Hydroxy-2-methylbut-2-enyl 4-Diphosphate, an Isoprenoid Precursor and Human γδ T Cell Activator

Covalent linking of poly(ethyleneglycol)‐bound NAD with Thermus thermophilus malate dehydrogenase

Photoinduced acyl transfer

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