scholarly journals Synthetic strategies of phosphonodepsipeptides

2021 ◽  
Vol 17 ◽  
pp. 461-484
Author(s):  
Jiaxi Xu
Keyword(s):  
Amino Acids ◽  
Enzyme Inhibitors ◽  
Biological Agents ◽  
Alkyl Halides ◽  
Multicomponent Condensation ◽  
Naturally Occurring ◽  
Carbene Insertion ◽  
Hydroxy Esters

Phosphonodepsipeptides are phosphorus analogues of depsipeptides and phosphonate-linked analogues of naturally occurring peptides. They are more stable than phosphonopeptides and have been widely applied as enzyme inhibitors, haptens for the production of antibodies, biological agents, and prodrugs. The synthetic strategies towards phosphonodepsipeptides are reviewed, including the phosphonylation of hydroxy esters with phosphonochloridates, the condensation of phosphonic monoesters and hydroxy esters, the alkylation of phosphonic monoesters with 1-(alkoxycarbonyl)alkyl halides or sulfonates, multicomponent condensation of amides, aldehydes, and dichlorophosphites followed by alcoholysis with hydroxy esters, the phosphinylation of hydroxy esters with phosphonochloridites followed by oxidation, and the carbene insertion of N-protected amino acids with 1-diazoalkylphosphonates. This review includes the synthesis of α-, β-, and γ-phosphonodepsipeptides and phosphonodepsipeptides with C-1-hydroxyalkylphosphonic acids.

Use of inhibitors to study reactions catalyzed by enzymes requiring pyridoxal phosphate as coenzyme

2000 ◽  
Vol 72 (3) ◽  
pp. 373-384 ◽  
Author(s):  
Benjamin Adams ◽  
B. Svante Axelsson ◽  
Kenneth J. M. Beresford ◽  
Nicola J. Church ◽  
Philip A. Spencer ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Active Site ◽  
Aspartate Aminotransferase ◽  
Pyridoxal Phosphate ◽  
Family Formation ◽  
Enzyme Inhibitors ◽  
Acid Oxidase ◽  
Amino Acid Oxidase ◽  
Naturally Occurring

The stereochemistry of a variety of pyridoxal phosphate-mediated enzymic reactions has been studied using enzyme inhibitors that are stereospecifically labeled in the β-position with deuterium. A versatile synthesis has been developed to prepare a wide variety of stereospecifically labeled d- and l-amino acids and inhibitors. Investigation of the "turnover" of β-chloro-d-alanine and d- and l-serine-O-sulfate by d-amino acid aminotransferase and l-aspartate aminotransferase respectively has shown that reaction within the active site of the former enzyme occurs with retention of stereochemistry. Although l-aspartate aminotransferase is an enzyme of the α-family, when it was incubated with β-chloro-l-alanine in the presence of 2-mercaptoethanol, β-substitution occurred. This was shown to involve retention of stereochemistry, an outcome typical of reactions catalyzed by enzymes of the β-family that have little or no homology with enzymes of the α-family. Formation of the "Schnackerz intermediate" has been studied as has the d-amino acid oxidase catalyzed reaction of the naturally occurring inhibitor d-propargylglycine.

scholarly journals Regulation of rat magnocellular neurosecretory system by D-aspartate: evidence for biological role(s) of a naturally occurring free D-amino acid in mammals

2000 ◽  
Vol 167 (2) ◽  
pp. 247-252 ◽  
Author(s):  
H Wang ◽  
H Wolosker ◽  
J Pevsner ◽  
SH Snyder ◽  
DJ Selkoe
Keyword(s):  
Gene Expression ◽  
Amino Acids ◽  
Amino Acid ◽  
Physiological Function ◽  
Neurosecretory System ◽  
Milk Ejection ◽  
Magnocellular Neurons ◽  
Rat Hypothalamus ◽  
Naturally Occurring

Little evidence is available for the physiological function of D-amino acids in species other than bacteria. Here we demonstrate that naturally occurring freed -aspartate (D-Asp) is present in all magnocellular neurons of rat hypothalamus. The levels of this naturally occurring D-amino acid were elevated during lactation and returned to normal thereafter in the magnocellular neurosecretory system, which produces oxytocin, a hormone responsible for milk ejection during lactation. Intraperitoneal injections of D-Asp reproducibly increased oxytocin gene expression and decreased the concentration of circulating oxytocin in vivo. Similar changes were observed in the vasopressin system. These results provide evidence for the role(s) of naturally occurring free D-Asp in mammalian physiology. The findings argue against the conventional concept that only L-stereoisomers of amino acids are functional in higher species.

Adsorption of carbon dioxide on naturally occurring solid amino acids

2016 ◽  
Vol 4 (3) ◽  
pp. 3170-3176 ◽  
Author(s):  
Sreedipta Chatterjee ◽  
Sadhana Rayalu ◽  
Spas D. Kolev ◽  
Reddithota J. Krupadam
Keyword(s):  
Carbon Dioxide ◽  
Amino Acids ◽  
Naturally Occurring

scholarly journals Transporters in Arabidopsis roots mediating uptake of amino acids at naturally occurring concentrations

2011 ◽  
Vol 191 (2) ◽  
pp. 459-467 ◽  
Author(s):  
Henrik Svennerstam ◽  
Sandra Jämtgård ◽  
Iftikhar Ahmad ◽  
Kerstin Huss-Danell ◽  
Torgny Näsholm ◽  
...  
Keyword(s):  
Amino Acids ◽  
Naturally Occurring

Effects of some Amino-acid and Purine Antagonists on Chick Embryos

Development ◽  
1958 ◽  
Vol 6 (2) ◽  
pp. 365-372
Author(s):  
C. H. Waddington ◽  
Margaret Perry
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Effective Concentration ◽  
Metabolic Inhibitors ◽  
Chick Embryos ◽  
Purine Analogue ◽  
Know How ◽  
Naturally Occurring ◽  
Different Types ◽  
Strong Action

Several authors have studied the effects on developing embryos of substances which are analogues of naturally occurring amino-acids and purines, and known to act, in other systems, as metabolic inhibitors. It was emphasized by Waddington, Feldman, & Perry (1955) that any particular substance may exhibit very different effects in embryos of different types. They found, for instance, that the purine analogue 8-azaguanine has a very strong action in the chick and a much lesser one in the newt embryo. It is therefore necessary to consider the various classes of embryos separately. In this communication we shall be concerned only with chick embryos. Substances under test can be administered to such embryos by injection through the shell, as was done in the paper cited above With this technique it is impossible to know how much diffusion takes place of the substance injected, and one cannot therefore be certain of the effective concentration which actually reaches the embryo.

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