130096-70-7Relevant academic research and scientific papers
Continuous-flow thermolysis for the preparation of vinylglycine derivatives
Lamborelle, Nicolas,Simon, Justine F.,Luxen, André,Monbaliu, Jean-Christophe M.
, p. 11602 - 11606 (2015/12/08)
Syn sulfoxide elimination was carried out under continuous-flow conditions in a mesofluidic thermolysis reactor. The design of the reactor enabled accurate control of reaction time and conditions, affording a convenient scale-independent procedure for the production of N,C-protected vinylglycine derivatives. Thermolysis at 270 °C under 1000 psi of pressure in superheated toluene enabled typical daily outputs ranging from 11 to 46 g per day with excellent selectivities and ee (>97%). The various competitive reaction pathways were studied and rationalized according to a computational study.
Glutathione-analogous peptidyl phosphorus esters as mechanism-based inhibitors of γ-glutamyl transpeptidase for probing cysteinyl-glycine binding site
Nakajima, Mado,Watanabe, Bunta,Han, Liyou,Shimizu, Bun-Ichi,Wada, Kei,Fukuyama, Keiichi,Suzuki, Hideyuki,Hiratake, Jun
supporting information, p. 1176 - 1194 (2014/02/14)
γ-Glutamyl transpeptidase (GGT) catalyzing the cleavage of γ-glutamyl bond of glutathione and its S-conjugates is involved in a number of physiological and pathological processes through glutathione homeostasis Defining its Cys-Gly binding site is extremely important not only in defining the physiological function of GGT, but also in designing specific and effective inhibitors for pharmaceutical purposes Here we report the synthesis and evaluation of a series of glutathione-analogous peptidyl phosphorus esters as mechanism-based inhibitors of human and Escherichia coli GGTs to probe the structural and stereochemical preferences in the Cys-Gly binding site Both enzymes were inhibited strongly and irreversibly by the peptidyl phosphorus esters with a good leaving group (phenoxide) Human GGT was highly selective for l-aliphatic amino acid such as l-2-aminobutyrate (l-Cys mimic) at the Cys binding site, whereas E coli GGT significantly preferred l-Phe mimic at this site The C-terminal Gly and a l-amino acid analogue at the Cys binding site were necessary for inhibition, suggesting that human GGT was highly selective for glutathione (γ-Glu-l-Cys-Gly), whereas E coli GGT are not selective for glutathione, but still retained the dipeptide (l-AA-Gly) binding site The diastereoisomers with respect to the chiral phosphorus were separated Both GGTs were inactivated by only one of the stereoisomers with the same stereochemistry at phosphorus The strict recognition of phosphorus stereochemistry gave insights into the stereochemical course of the catalyzed reaction Ion-spray mass analysis of the inhibited E coli GGT confirmed the formation of a 1:1 covalent adduct with the catalytic subunit (small subunit) with concomitant loss of phenoxide, leaving the peptidyl moiety that presumably occupies the Cys-Gly binding site The peptidyl phosphonate inhibitors are highly useful as a ligand for X-ray structural analysis of GGT for defining hitherto unidentified Cys-Gly binding site to design specific inhibitors
The synthesis of diaminopimelic acid containing peptidoglycan fragments using metathesis cross coupling
Chowdhury, Abhijit Roy,Boons, Geert-Jan
, p. 1675 - 1678 (2007/10/03)
Properly protected diaminopimelic acid (DAP), a component of peptidoglycan of Gram-negative bacteria, was prepared by a metathesis cross coupling between properly protected allyl and vinyl glycine derivatives using Grubb's second-generation catalyst follo
C-linked galactosyl serine AFGP analogues as potent recrystallization inhibitors
Liu, Suhuai,Ben, Robert N.
, p. 2385 - 2388 (2007/10/03)
(Chemical Equation Presented) A series of C-linked antifreeze glycoprotein analogues have been prepared to evaluate antifreeze activity as a function of distance between the carbohydrate moiety and polypeptide backbone. The building blocks for these analogues were prepared using either an olefin cross-metathesis or catalytic asymmetric hydrogenation. Analysis of antifreeze protein-specific activity revealed that only analogue 2a (n = 1) was a potent recrystallization inhibitor and thus has potential medical and industrial applications.
Isoxazoline and isoxazole fibrinogen receptor antagonists
-
, (2008/06/13)
This invention relates to novel isoxazolines and isoxazoles which are useful as antagonists of the platelet glycoprotein IIb/IIIa fibrinogen receptor complex or the vitronectin receptor, to pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.
Stereochemical Correlation of Proclavamimic Acid and Syntheses of erythro- and threo-L-β-Hydroxyornithine from an Improved Vinylglycine Synthone
Krol, Walter J.,Mao, Shin-shan,Steele, Diana L.,Townsend, Craig A.
, p. 728 - 731 (2007/10/02)
The Hanessian method to prepare the N-Cbz-L-vinylglycine methyl ester has been improved to obtain reproducibility an alternately protected version of this useful synthon in optically pure, crystalline form.A nitrone cycloaddition route has been developed
