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.

Optical Resolution of α-Amino Acids by Reverse Osmosis using Enantioselective Polymer Membrane Containing Chiral Metal-Schiff Base Complex

2010 ◽  
Vol 45 (10) ◽  
pp. 1374-1384 ◽  
Author(s):  
Kripal Singh ◽  
Pravin G. Ingole ◽  
H. C. Bajaj ◽  
Amit Bhattacharya ◽  
Harshad R. Brahmbhatt
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Reverse Osmosis ◽  
Optical Resolution ◽  
Schiff Base Complex ◽  
Polymer Membrane ◽  
Base Complex

scholarly journals A new synthesis of enantiomerically pure syn-(S)-β-hydroxy-α-amino acids via asymmetric aldol reactions of aldehydes with a homochiral Ni(II)-glycine/(S)-BPB Schiff base complex

2001 ◽  
Vol 12 (3) ◽  
pp. 481-485 ◽  
Author(s):  
Yuri N. Belokon ◽  
Konstantin A. Kochetkov ◽  
Nikolai S. Ikonnikov ◽  
Tatiana V. Strelkova ◽  
Syuzanna R. Harutyunyan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Schiff Base Complex ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Enantiomerically Pure ◽  
Base Complex ◽  
New Synthesis

Catalytic Asymmetric Synthesis of Nitrogen-Containing gem-Bisphosphonates Using a Dinuclear Ni2-Schiff Base Complex

Synlett ◽  
2009 ◽  
Vol 2009 (10) ◽  
pp. 1635-1638 ◽  
Author(s):  
Shigeki Matsunaga ◽  
Masakatsu Shibasaki ◽  
Yuko Kato ◽  
Zhihua Chen
Keyword(s):  
Schiff Base ◽  
Asymmetric Synthesis ◽  
Schiff Base Complex ◽  
Base Complex ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric

ChemInform Abstract: A New Synthesis of Enantiomerically Pure syn-(S)-β-Hydroxy-α-amino Acids via Asymmetric Aldol Reactions of Aldehydes with a Homochiral Ni(II)-Glycine/(S)-BPB Schiff Base Complex.

ChemInform ◽  
2010 ◽  
Vol 32 (29) ◽  
pp. no-no
Author(s):  
Yuri N. Belokon ◽  
Konstantin A. Kochetkov ◽  
Nikolai S. Ikonnikov ◽  
Tatiana V. Strelkova ◽  
Syuzanna R. Harutyunyan ◽  
...  
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Schiff Base Complex ◽  
Aldol Reactions ◽  
Asymmetric Aldol ◽  
Enantiomerically Pure ◽  
Base Complex ◽  
New Synthesis

Stereoselective interaction of a tridentate Schiff base complex of nickel(II) and amino acids

1979 ◽  
Vol 57 (8) ◽  
pp. 883-885 ◽  
Author(s):  
B. Erno ◽  
R. B. Jordan
Keyword(s):  
Amino Acids ◽  
Schiff Base ◽  
Amino Acid ◽  
Schiff Base Complex ◽  
Salt Crystallization ◽  
Sensitive Test ◽  
Dilute Acid ◽  
Base Complex ◽  
Tridentate Schiff Base ◽  
Perchlorate Salt

It has been observed that a tridentate Schiff base complex of nickel(II), triaquotribenzo-[b,f,j][1.5.9]-triazacyclodecinenickel(II), commonly called (TRI)Ni(OH2)32+, shows substantial stereoselectivity on complexing with several amino acids. This provides a convenient way to resolve (TRI)Ni(OH2)32+ using histidine as a resolving agent, and either ion exchange or perchlorate salt crystallization techniques.The resolved (TRI)Ni(OH2)32+ may then be used to resolve other amino acids or as a sensitive test of the stereochemistry of an amino acid. The test can be done on milligram quantities because of the insolubility of the complex perchlorate salt and because of the relatively large molecular rotation (2 × 105 deg at 283 nm) of (TRI)Ni(OH2)32+. The amino acid is easily released by treatment of the complex with dilute acid (Ph ≈ 2). The procedure has been tested with histidine, tyrosine, methionine, and phenylglycine.

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