127515-28-0Relevant articles and documents
Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal α-addition of allylboronates to hydrazono esters
Fujita, Mari,Nagano, Takashi,Schneider, Uwe,Hamada, Tomoaki,Ogawa, Chikako,Kobayashi, Shu
, p. 2914 - 2915 (2008/10/09)
We have developed Zn-catalyzed asymmetric allylation of hydrazono esters with allylboronates. The reactions proceeded smoothly in high yields and high stereoselectivities. Remarkably, formal α-addition occurred for α-substituted allylboronates exclusively, and excellent stereoselectivities were observed. This is the first example of catalytic regio- and stereoselective allylations with formal α-addition. In addition, the reaction proceeded in aqueous media, and the use of water is essential. Zn(OH)2 might be a catalyst in this asymmetric allylation, and the catalytic activity of Zn(OH)2 was confirmed. This is also the first case of chiral metal hydroxide-catalyzed asymmetric reactions. Copyright
Resolution of non-proteinogenic amino acids via microbial lipase-catalyzed enantioselective transesterification
Miyazawa, Toshifumi,Mio, Motoe,Watanabe, Yuko,Yamada, Takashi
, p. 219 - 224 (2008/09/20)
A number of non-proteinogenic amino acids bearing aliphatic side chains were resolved with moderate to good enantioselectivities (E = 15-42) through the Burkholderia cepacia lipase-catalyzed enantioselective transesterification of the 2,2,2-trifluoroethyl esters of their N-benzyloxycarbonyl derivatives with methanol as a nucleophile in diisopropyl ether.
Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome
Barluenga, Sofia,Simonsen, Klaus B.,Littlefield, Ethel S.,Ayida, Benjamin K.,Vourloumis, Dionisios,Winters, Geoffrey C.,Takahashi, Masayuki,Shandrick, Sarah,Zhao, Qiang,Han, Qing,Hermann, Thomas
, p. 713 - 718 (2015/02/06)
RNA recognition by natural aminoglycoside antibiotics depends on the 2-deoxystreptamine (2-DOS) scaffold which participates in specific hydrogen bonds with the ribosomal decoding-site target. Three-dimensional structure information has been used for the design of azepane-monoglycosides, building blocks for novel antibiotics in which 2-DOS is replaced by a heterocyclic scaffold. Azepane-glycosides showed target binding and translation inhibition in the low micromolar range and inhibited growth of Staphylococcus aureus, including aminoglycoside-resistant strains.
Use of hydrolases for the synthesis of cyclic amino acids
Lloyd, Richard C.,Lloyd, Michael C.,Smith, Mark E. B.,Holt, Karen E.,Swift, Jonathan P.,Keene, Philip A.,Taylor, Stephen J. C.,McCague, Raymond
, p. 717 - 728 (2007/10/03)
The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. I
Chemoenzymatic synthesis of the four diastereoisomers of 4-hydroxypipecolic acid from N-acetyl-(R,S)-allylglycine: Chiral scaffolds for drug discovery
Lloyd, Richard C.,Smith, Mark E. B.,Brick, Dean,Taylor, Stephen J. C.,Chaplin, David A.,McCague, Raymond
, p. 762 - 766 (2013/09/06)
All four diastereoisomers of 4-hydroxypipecolic acid were prepared in a form conveniently protected for drug discovery applications with the use of industrially scaleable methodology. Resolution of the racemic starting material using proprietary acylases followed by an acyliminium ion cyclisation gave diastereomeric mixtures of 4-formyloxypipecolic acid, which were differentiated using an enzyme-catalysed hydrolysis. The products were separated by partition, and by following a sequence of straightforward chemical steps, the individual stereoisomers of the protected 4-hydroxypipecolates were crystallized to optical purity in 100 g quantities.
Synthesis of (Optically Active) Sulfur-Containing Trifunctional Amino Acids by Radical Addition to (Optically Active) Unsaturated Amino Acids
Broxterman, Quirinus B.,Kaptein, Bernard,Kamphuis, Johan,Schoemaker, Hans E.
, p. 6286 - 6294 (2007/10/02)
Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to α-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H).Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100 percent).The solvent used for the reaction is critical.Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems).The scope of the reaction includes α-substituted α-allylglycine derivative and derivatives as well as β-substituted β-allyl-β-amino alcohols.In the case of optically active α-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H.The products are easily optically enriched by crystallization.Addition of sulfur-based radicals to α-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.
Synthesis, absolute configuration and activity at N-methyl-D-aspartic acid (NMDA) receptor of the four D-2-amino-4,5-methano-adipate diastereoisomers
Pellicciari,Natalini,Marinozzi,Sadeghpour,Cordi,Lanthorn,Hood,Monahan
, p. 1243 - 1264 (2007/10/02)
The four D-2-amino-4,5-methano-adipates 26, 27, 32, 33 were synthesized and their biological activity at the N-methyl-D-aspartate (NMDA) receptor was assessed. The synthesis involved as a key step a rhodium acetate dimer catalyzed addition of ethyl diazoacetate to the protected D-allylglycine (17). In vitro receptor binding using L-[3H]glutamate as the radioligand provided affinity data, while modulation of [3H]TCP binding was used as a functional assay. The analogues were also evaluated in [3H]kainate and [3H]AMPA binding to assess selectivity over non-NMDA glutamate receptors. Three of the four diastereoisomer, D-CAA B (27), C (32) and D (33) were shown to have agonist properties at the NMDA-site, while the fourth, (2R,4R,5R) D-CAA A (26) was characterized as an NMDA-site atypic antagonist.
