1H, 13C and 15N NMR Spectra of Ni(II) Complex of Schiff Base from (S)-2-(N-Benzylprolyl)amino-5-methylbenzophenone and Glycine

1994 ◽  
Vol 59 (9) ◽  
pp. 2103-2108 ◽  
Author(s):  
Josef Jirman ◽  
Alexander Popkov
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Nmr Spectra ◽  
15N Nmr ◽  
Nmr Signals

Nickel(II) complex of Schiff base derived from (S)-2-(N-benzylprolyl)amino-5-methylbenzophenone and glycine (I) was prepared. It was characterized by mass, 1H, 13C and 15N NMR spectra. The NMR signals were assigned and the data thus obtained can serve for study of products in the asymmetric synthesis of amino acids, starting from this complex.

General method for the asymmetric synthesis of α-amino acids via alkylation of the chiral nickel(II) Schiff base complexes of glycine and alanine

1988 ◽  
pp. 305-312 ◽  
Author(s):  
Yuri. N. Belokon ◽  
Vladimir I. Bakhmutov ◽  
Nina I. Chernoglazova ◽  
Konstantin A. Kochetkov ◽  
Sergei V. Vitt ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Schiff Base Complexes ◽  
General Method

Robust asymmetric synthesis of unnatural alkenyl amino acids for conformationally constrained α-helix peptides

2014 ◽  
Vol 12 (43) ◽  
pp. 8775-8782 ◽  
Author(s):  
Boris Aillard ◽  
Naomi S. Robertson ◽  
Adam R. Baldwin ◽  
Siobhan Robins ◽  
Andrew G. Jamieson
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Schiff Base Complex ◽  
Conformationally Constrained ◽  
Base Complex ◽  
Α Helix ◽  
Peptide Stapling

The efficient asymmetric synthesis of unnatural alkenyl amino acids required for peptide ‘stapling’ has been achieved using alkylation of a fluorine-modified NiII Schiff base complex as the key step.

1H, 13C, and 15N NMR Spectra of Ni(II) Complexes of Schiff Bases of (S)-2-(N-Benzylprolyl)aminobenzophenone and α-Monosubstituted Glycine and Determination of Configuration of the Complexes by 2D NOESY Spectra

1995 ◽  
Vol 60 (6) ◽  
pp. 990-998 ◽  
Author(s):  
Josef Jirman ◽  
Alexander Popkov
Keyword(s):  
Schiff Base ◽  
Schiff Bases ◽  
Absolute Configuration ◽  
Nmr Spectra ◽  
Phenyl Group ◽  
15N Nmr ◽  
Dimethylamino Group ◽  
2D Noesy ◽  
Noesy Spectra

1H, 13C, and 15N NMR spectra have been measured of substituted Ni(II) complexes of Schiff bases of (S)-2-(N-benzylprolyl)aminobenzophenone and glycine. The absolute configuration at C19 of the substituted glycine can be determined from 2D NOESY spectra using the NOESY interactions with the proton of the second chiral centre of the complex. It is possible to determine the rate of rotation of phenyl group of benzophenone unless its rotation is prevented by requatorialr orientation of dimethylamino group as it is the case with the Ni(II) complex of Schiff base of (S)-2-(N-benzylprolyl)aminobenzophenone and (S)-α-dimethylaminoglycine.

Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

2014 ◽  
Vol 69 (4) ◽  
pp. 451-460 ◽  
Author(s):  
Ashot S. Saghyan ◽  
Hayarpi M. Simonyan ◽  
Satenik G. Petrosyan ◽  
Anna F. Mkrtchyan ◽  
Lilit V. Khachatryan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Efficient Method ◽  
Enantiomeric Excess ◽  
Side Chain ◽  
Chiral Auxiliaries ◽  
Enantiomerically Pure ◽  
Dehydroamino Acids ◽  
Hydrolysis Of

An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

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