13893-53-3Relevant articles and documents
Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures
Islam, Saidul,Bu?ar, Dejan-Kre?imir,Powner, Matthew W.
, p. 584 - 589 (2017)
A central problem for the prebiotic synthesis of biological amino acids and nucleotides is to avoid the concomitant synthesis of undesired or irrelevant by-products. Additionally, multistep pathways require mechanisms that enable the sequential addition of reactants and purification of intermediates that are consistent with reasonable geochemical scenarios. Here, we show that 2-aminothiazole reacts selectively with two- and three-carbon sugars (glycolaldehyde and glyceraldehyde, respectively), which results in their accumulation and purification as stable crystalline aminals. This permits ribonucleotide synthesis, even from complex sugar mixtures. Remarkably, aminal formation also overcomes the thermodynamically favoured isomerization of glyceraldehyde into dihydroxyacetone because only the aminal of glyceraldehyde separates from the equilibrating mixture. Finally, we show that aminal formation provides a novel pathway to amino acids that avoids the synthesis of the non-proteinogenic α,α-disubstituted analogues. The common physicochemical mechanism that controls the proteinogenic amino acid and ribonucleotide assembly from prebiotic mixtures suggests that these essential classes of metabolite had a unified chemical origin.
Recyclable Enantioselective Catalysts Based on Copper(II) Complexes of 2-(Pyridine-2-yl)imidazolidine-4-thione: Their Application in Asymmetric Henry Reactions
Nováková, Gabriela,Drabina, Pavel,Frumarová, Bo?ena,Sedlák, Milo?
supporting information, p. 2541 - 2552 (2016/08/16)
This paper describes the preparation of enantioselective catalysts based on derivatives of imidazolidine-4-thione and their subsequent anchoring by means of a sulfur atom on a polymeric carrier. First, we verified the catalytic activity and enantioselecti
Synthesis of enantiopure fmoc-#-methylvaline
Shu, Lianhe,Wang, Ping
, p. 298 - 300 (2013/01/03)
An efficient synthesis of enantiopure Fmoc-α-methylvaline has been developed. The racemate was prepared in two steps from 3-methyl-2-butanone and was resolved using a chiral amine, (S)- 1,2,3,4-tetrahydro-1-naphthylamine to give the desired, enantiopure S