31571-69-4Relevant academic research and scientific papers
Indium-mediated allylation and Reformatsky reaction on glyoxylic oximes under ultrasound irradiation
Soengas, Raquel G.,Estévez, Amalia M.
experimental part, p. 916 - 920 (2012/06/04)
A novel and more convenient method for the indium-promoted allylation of glyoxylic oximes based on the use of ultrasonic waves is reported. A similar procedure was used to develop the first example reported in the literature of an indium-mediated Reformatsky reaction on oxime ethers.
Peculiar stability of amino acids and peptides from a radical perspective
Watts, Zachary I.,Easton, Christopher J.
supporting information; experimental part, p. 11323 - 11325 (2011/03/19)
(Chemical Equation Presented) Photochemical reactions of free and N-acetyl α-amino acids with chlorine and deuterium labeled hydrogen peroxide have been used to determine both the relative rates of reaction of molecules of these classes and the relative reactivity of their different types of hydrogen toward abstraction by chlorine and oxygen centered radicals. The relative rates of reaction of these species range over more than 3 orders of magnitude; however, where data are available from more than one amino acid for a particular type of group at a specific position on the side chain, the values are remarkably similar. The predictive utility of these results has been demonstrated for the regioselective chlorination of tripeptides. More generally this analysis shows that the backbone and adjacent side chain positions of amino acids and peptides are peculiarly resistant to hydrogen atom transfer, and a similar pattern of reactivity has been noted from earlier studies of reactions of modified substrates catalyzed by isopenicillin-N-synthetase. Such resistance stands out in contrast to the common occurrence of free radical reactions of α-amino acids, peptides, and proteins and their importance in biology. Nevertheless, it provides a reason for the ability of amino acids and their derivatives to avoid degradation in Nature where they are constantly exposed to radicals, and it accounts, at least in part, for the anomalous ability of enzymes to catalyze free radical reactions without being broken down by the radical intermediates.
Organocatalytic synthesis of β-alkylaspartates via β-lactone ring opening
Armstrong, Alan,Geldart, Stephen P.,Jenner, Chloe R.,Scutt, James N.
, p. 8091 - 8094 (2008/02/13)
(Chemical Equation Presented) Cinchona alkaloid-catalyzed reaction of ethyl glyoxylate with substituted ketenes, formed in situ, gives disubstituted β-lactones in moderate yield and high enantiomeric excess. Subsequent azide ring opening, reduction, and e
Ligands for metal affinity chromatography
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, (2008/06/13)
The invention provides a metal chelate resin that comprises repeating units having the structure: where M is a metal ion in an oxidation state capable of forming a complex with a tetradentate ligand having an overall coordination number of at least 6, R1,
Kinetics and Mechanism of syn-Elimination of Ammonia from (2S,3R)-3-Methylaspartic Acid by Methylaspartase
Archer, Catherine H.,Gani, David
, p. 140 - 142 (2007/10/02)
Methylaspartase catalyses the slow syn-elimination of ammonia from the (2S,3R)--diastereoisomer of the natural substrate (2S,3S)-3-methylaspartic acid, to give mesaconic acid; the reaction does not involve C-3 epimerisation followed by normal anti-elimination, ruling-out the possibility of a carbanion intermediate, but, displays large primary deuterium isotope effects consistent with concerted C-H and C-N bond cleavage.
SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN
Mori, Kenji,Nomi, Hiroko,Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao
, p. 3705 - 3712 (2007/10/02)
The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by
