105382-09-0Relevant articles and documents
An efficient asymmetric biomimetic transamination of α-keto esters to chiral α-amino esters
Xiao, Xiao,Liu, Mao,Rong, Chao,Xue, Fazhen,Li, Songlei,Xie, Ying,Shi, Yian
, p. 5270 - 5273 (2013/01/15)
An efficient asymmetric biomimetic transamination of α-keto esters with quinine derivatives as chiral bases was described. A wide variety of α-amino esters containing various functional groups can be synthesized in high yield and enantioselectivity.
New anthranilic acid based antagonists with high affinity and selectivity for the human cholecystokinin receptor 1 (hCCK1-R)
Pavan, Michela V.,Lassiani, Lucia,Berti, Federico,Stefancich, Giorgio,Ciogli, Alessia,Gasparrini, Francesco,Mennuni, Laura,Ferrari, Flora,Escrieut, Chantal,Marco, Esther,Makovec, Francesco,Fourmy, Daniel,Varnavas, Antonio
experimental part, p. 5769 - 5785 (2011/10/09)
The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.
Asymmetric and efficient synthesis of homophenylalanine derivatives via Friedel-Crafts reaction with trifluoromethanesulfonic acid
Murashige, Ryo,Hayashi, Yuka,Hashimoto, Makoto
supporting information; scheme or table, p. 6566 - 6568 (2009/04/05)
An efficient Friedel-Crafts reaction of TFA-Asp(Cl)-OMe and stoichiometric amounts of benzene was established by using neat trifluoromethanesulfonic acid (TfOH) as solvent and catalyst under a mild condition. This methodology has been applied to many arom
Asymmetric petasis reactions catalyzed by chiral biphenols
Lou, Sha,Schaus, Scott E.
, p. 6922 - 6923 (2008/09/21)
Chiral biphenols catalyze the enantioselective Petasis reaction of alkenyl boronates, secondary amines, and ethyl glyoxylate. The reaction requires the use of 15 mol % of (S)-VAPOL as the catalyst, alkenyl boronates as nucleophiles, ethyl glyoxylate as the aldehyde component, and 3 A molecular sieves as an additive. The chiral α-amino ester products are obtained in good yields (71-92%) and high enantiomeric ratios (89:11-98:2). Mechanistic investigations indicate single ligand exchange of acyclic boronate with VAPOL and tetracoordinate boronate intermediates. Copyright
Total synthesis of amiclenomycin, an inhibitor of biotin biosynthesis.
Mann, Stephane,Carillon, Sophie,Breyne, Olivier,Marquet, Andree
, p. 439 - 450 (2007/10/03)
We describe the first synthesis of amiclenomycin, a natural product that has been found to inhibit biotin biosynthesis and, as a consequence, to exhibit antibiotic properties. Structure 1, with a trans relationship between the ring substituents. had previously been proposed for amiclenomycin on the basis of its 1H NMR spectrum. We have prepared the trans and cis isomers 1 and 2 by unequivocal routes and we conclude that the natural product is in fact the cis isomer 2. The properly substituted cyclohexadienyl rings were constructed first. A cycloaddition reaction between 1,2-di(phenylsulfonyl)ethylene and the N-allyloxycarbonyl diene 13, followed by reductive elimination of the phenylsulfinyl groups, gave the cis isomer 15. To obtain the trans isomer, the O-trimethylsilyl diene was used to give the cis hydroxylated Diels-Alder adduct 33, which was transformed into the corresponding trans amino derivative by means of a Mitsunobu reaction. The L-alpha-amino acid functionality was introduced by means of a Strecker reaction on the aldehydes 16 and 42, followed by enzymatic hydrolysis with immobilised pronase.
Concise synthesis and enzymatic resolution of L-(+)-homophenylalanine hydrochloride
Zhao, Hua,Luo, Robert G.,Wei, Dean,Malhotra, Sanjay V.
, p. 1 - 3 (2007/10/03)
The N-acetyl-homophenylalanine ethyl ester was synthesized by a simple three-step-reaction strategy. L-(+)-homophenylalanine hydrochloride with 98% ee was obtained through a kinetic resolution process using industrial enzyme alcalase. Compared with other
The synthesis of L-(+)-homophenylalanine hydrochloride
Xu, Qianyong,Wang, Guoxin,Wang, Xuechao,Wu, Tongxing,Pan, Xinfu,Chan, Albert S.C.,Yang, Teng-Kuei
, p. 2309 - 2314 (2007/10/03)
L-(+)-Homophenylalanine hydrochloride was synthesized from N-phthaloyl-L-(-)-asparitc anhydride 2 in three steps in 55% overall yield with 99% ee. Copyright (C) 2000 Elsevier Science Ltd.
Asymmetric amino acid synthesis: Mitsunobu reaction on chiral cyanohydrins
Decicco, Carl P.,Grover, Paul
, p. 529 - 530 (2007/10/03)
BOC(SES)NH was reacted with chiral cyanohydrins using the Mitsunobu reaction to give good yields of protected α-aminonitriles, which were converted to chiral amino and imino acids.
Hexa- and heptapeptide anaphylatoxin-receptor ligands
-
, (2008/06/13)
Oligopeptide compounds or oligopeptide analogue compounds of the formula A-B-D-E-G-J-L-M-Q are ligands for the anaphylatoxin receptor and are useful in the treatment of inflammatory disease states.Also disclosed are anaphylatoxin receptor ligand compositi