105024-93-9Relevant articles and documents
Improved procedures for the synthesis of (S)-2-[N-(N'-benzyl- prolyl)amino]benzophenone (BPB) and Ni(II) complexes of Schiff's bases derived from BPB and amino acids
Belokon', Yuri N.,Tararov, Vitali I.,Maleev, Viktor I.,Savel'eva, Tatiana F.,Ryzhov, Michael G.
, p. 4249 - 4252 (1998)
(S)-N-Benzylproline (BP) was obtained by the reaction of (S)-proline and benzylchloride in high chemical yield (89%). (S)-2-[N-(N'- Benzylprolyl)amino]benzophenone (BPB) was synthesized in amounts greater than 100 g by the SOCl2 promoted condensation of BP with 2-aminobenzophenone (yield 82%). Ni(II) complexes of Schiff's bases derived from BPB and amino acids were prepared by an improved procedure involving the use of KOH as a base and MeOH as solvent (yield 90-91%).
Enantioselective synthesis of 2-substitued-tetrahydroisoquinolin-1-yl glycine derivatives via oxidative cross-dehydrogenative coupling of tertiary amines and chiral nickel(II) glycinate
Zhou, Shengbin,Wang, Jiang,Lin, Daizong,Zhao, Fei,Liu, Hong
, p. 11204 - 11212 (2013)
The asymmetric synthesis of 2-substituted-tetrahydroisoquinolin-1-yl glycines was achieved by an oxidative cross-dehydrogenative coupling (CDC) reaction. This method for activation of the α-C-H bonds of amines with chiral nickel(II) glycinate using o-chlo
ASYMMETRIC SYNTHESIS OF ASPARTIC AND α-METHYLASPARTIC ACIDS VIA Ni(II) COMPLEXES WITH SCHIFF BASES OF GLYCINE AND ALANINE AND CHIRAL CARBONYL-CONTAINING REAGENTS
Belokon, Yu. N.,Tararov, V. I.,Maleev, V. I.,Motsishkite, S. M.,Vitt, S. V.,et al.
, p. 1361 - 1365 (1991)
We propose a method for the synthesis of aspartic and α-methylaspartic acids by alkylation with ethyl bromoacetate of the α-carbon atom of the amino acid moiety in Ni(II) complexes of Schiff bases of glycine with (S)-2-benzophenone and alanine with (S)-2-benzaldehyde, respectively.Attempts to synthesize α-methylaspartic acid by oxidative cleavage of the C=C bond to a COOH group in the complex of the Schiff base of α-allylalanine with (S)-2-benzophenone were unsuccessful.
Rational Design and Synthesis of Modified Teixobactin Analogues: In Vitro Antibacterial Activity against Staphylococcus aureus, Propionibacterium acnes and Pseudomonas aeruginosa
Ng, Vivian,Kuehne, Sarah A.,Chan, Weng C.
, p. 9136 - 9147 (2018)
Teixobactin, a recently discovered depsipeptide that binds to bacterial lipid II and lipid III, provides a promising molecular scaffold for the design of new antimicrobials. Herein, we describe the synthesis and antimicrobial evaluation of systematically modified teixobactin analogues. The replacement of the Ile11 residue with aliphatic isosteres, the modification of the guanidino group at residue 10 and the introduction of a rigidifying residue, that is, dehydroamino acid, into the macrocyclic ring generated useful structure–activity information. Extensive antimicrobial susceptibility assessment against a panel of clinically relevant Staphylococcus aureus and Propionibacterium acnes strains led to the identification of the new lead compound, [Arg(Me)10,Nle11]teixobactin, with an excellent bactericidal activity (minimum inhibitory concentration (MIC)=2–4 μg mL?1). Significantly, the antimicrobial activity of several of the teixobactin analogues against the pathogenic Gram-negative Pseudomonas aeruginosa was “restored” when combined with the sub-MIC concentration of the outer membrane-disruptive antibiotic colistin. The antimicrobial effectiveness of a [Tfn10,Nle11]teixobactin (32 μg mL?1)–colistin (2 μg mL?1; 0.5×MIC) combination against P. aeruginosa PAO1 reveals, for the first time, an alternative therapeutic option in the treatment of Gram-negative infections.
Asymmetric Synthesis of (2S,3S)-α-(1-Oxoisoindolin-3-yl)glycines under Low-Basicity "kinetic" Control
Li, Tingting,Zhou, Shengbin,Wang, Jiang,Ace?a, José Luis,Soloshonok, Vadim A.,Liu, Hong
, p. 11275 - 11280 (2015)
The previously illusive (2S,3S)-configured α-(1-oxoisoindolin-3-yl)glycines can be prepared under mild DBU-catalyzed, low-basicity conditions. The overall process includes a cascade of aldol addition, cyclization, rearrangement, and conjugate addition reactions, leading to the target products with moderate to good chemical yields and diastereoselectivity.
Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2-SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex
Kawashima, Aki,Xie, Chen,Mei, Haibo,Takeda, Ryosuke,Kawamura, Akie,Sato, Tatsunori,Moriwaki, Hiroki,Izawa, Kunisuke,Han, Jianlin,Acea, Jos Luis,Soloshonok, Vadim A.
, p. 1051 - 1058 (2015)
This work describes a new process for the asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid of high pharmaceutical importance. The sequence of the reactions includes PTC alkylation (SN2), homogeneous SN2′ cyclization followed by disassembly of the resultant Ni(ii) complex. All reactions are conducted under operationally convenient conditions and suitably scaled up to 6 g of the starting Ni(ii) complex. This journal is
Preparation of labeled aromatic amino acids: Via late-stage18F-fluorination of chiral nickel and copper complexes
Craig, Austin,Kolks, Niklas,Urusova, Elizaveta A.,Zischler, Johannes,Brugger, Melanie,Endepols, Heike,Neumaier, Bernd,Zlatopolskiy, Boris D.
supporting information, p. 9505 - 9508 (2020/09/03)
A general protocol for the preparation of 18F-labeled AAAs and α-methyl-AAAs applying alcohol-enhanced Cu-mediated radiofluorination of Bpin-substituted chiral complexes using Ni/Cu-BPX templates as double protecting groups is reported. The chiral auxiliaries are easily accessible from commercially available starting materials in a few synthetic steps. The versatility of the method was demonstrated by the high-yielding preparation of a series of [18F]F-AAAs and the successful implementation of the protocol into automated radiosynthesis modules. This journal is
Synthesis of Chiral Spin-Labeled Amino Acids
Vuong, Wayne,Mosquera-Guagua, Fabricio,Sanichar, Randy,McDonald, Tyler R.,Ernst, Oliver P.,Wang, Lei,Vederas, John C.
supporting information, p. 10149 - 10153 (2019/12/24)
Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.