An Improved and Green Preparation of 3-(Alkylthio)propionic Acids

Vaismaa, Matti J. P.; Yliniemelä, Sanna M.; Lajunen, Marja

doi:10.1515/znb-2007-1014

Cited by 4 publications

(2 citation statements)

References 16 publications

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“…[15] During our studies, we observed that an increase in the reaction temperature clearly greater than 100 C significantly accelerated the condensation. Our experiences related to the synthetic applications of microwave activation [17] encouraged us to study the effect of microwaves on this condensation reaction. In addition, the use of the closed microwave vessel would also help avoid moisture.…”

Section: Resultsmentioning

confidence: 99%

Microwave-Assisted One-Carbon Chain Extension in the Preparation of Terminal α-Hydroxy Ketones

Vaismaa

Leskinen

Lajunen

2009

Synthetic Communications

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The microwave-assisted synthesis of terminal a-hydroxy ketones from acid chlorides and tris(trimethylsiloxy)ethylene in the presence of triethylamine is reported. The use of triethylamine had several advantages in the reaction: it increased the reactivity of the acid chloride, acted as a scavenger of the HCl that was produced in the reaction, protected the silylated enol from decomposition, and made the excess use of the silyl reagent unnecessary. Mechanistic effects of triethylamine are discussed. Effects of various base additives, reaction temperatures, reaction times, and solvents in the reaction are compared.

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Section: Resultsmentioning

confidence: 99%

Microwave-Assisted One-Carbon Chain Extension in the Preparation of Terminal α-Hydroxy Ketones

Vaismaa

Leskinen

Lajunen

2009

Synthetic Communications

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“…The synthesis of 3-(propylthio)propionic acid was carried out as described by Vaismaa et al (2007). The oxidation of 3-(propylthio)propionic acid to P3SP was carried out as follows.…”

Section: Synthesis Of 3-(propylsulfonyl)propionic Acid (P3sp)mentioning

confidence: 99%

Crystallographic binding studies with an engineered monomeric variant of triosephosphate isomerase

Salin¹,

Kapetaniou²,

Vaismaa³

et al. 2010

Acta Crystallogr D Biol Cryst

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Crystallographic binding studies have been carried out to probe the active-site binding properties of a monomeric variant (A-TIM) of triosephosphate isomerase (TIM). These binding studies are part of a structure-based directed-evolution project aimed towards changing the substrate specificity of monomeric TIM and are therefore aimed at finding binders which are substrate-like molecules. A-TIM has a modified more extended binding pocket between loop-7 and loop-8 compared with wild-type TIM. The A-TIM crystals were grown in the presence of citrate, which is bound in the active site of each of the two molecules in the asymmetric unit. In this complex, the active-site loops loop-6 and loop-7 adopt the closed conformation, similar to that observed in liganded wild-type TIM. Extensive crystal-soaking protocols have been developed to flush the bound citrate out of the active-site pocket of both molecules and the crystal structure shows that the unliganded open conformation of the A-TIM active site is the same as in unliganded wild-type TIM. It is also shown that sulfonate compounds corresponding to the transition-state analogue 2-phosphoglycolate bind in the active site, which has a closed conformation. It is also shown that the new binding pocket of A-TIM can bind 3-phosphoglycerate (3PGA; an analogue of a C4-sugar phosphate) and 4-phospho-D-erythronohydroxamic acid (4PEH; an analogue of a C5-sugar phosphate). Therefore, these studies have provided a rationale for starting directed-evolution experiments aimed at generating the catalytic properties of a C5-sugar phosphate isomerase on the A-TIM framework.

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ChemInform Abstract: An Improved and Green Preparation of 3‐(Alkylthio)propionic Acids.

2007

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An Improved and Green Preparation of 3-(Alkylthio)propionic Acids

Cited by 4 publications

References 16 publications

Microwave-Assisted One-Carbon Chain Extension in the Preparation of Terminal α-Hydroxy Ketones

Microwave-Assisted One-Carbon Chain Extension in the Preparation of Terminal α-Hydroxy Ketones

Crystallographic binding studies with an engineered monomeric variant of triosephosphate isomerase

ChemInform Abstract: An Improved and Green Preparation of 3‐(Alkylthio)propionic Acids.

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