Asymmetric synthesis of .alpha.-amino acids. I. A new approach

1970 ◽  
Vol 92 (8) ◽  
pp. 2476-2488 ◽  
Author(s):  
Elias J. Corey ◽  
Ronald J. McCaully ◽  
Harbans S. Sachdev
ChemInform ◽  
2003 ◽  
Vol 34 (48) ◽  
Author(s):  
Ahmed M. Hafez ◽  
Travis Dudding ◽  
Ty R. Wagerle ◽  
Meha H. Shah ◽  
Andrew E. Taggi ◽  
...  

2004 ◽  
Vol 59 (4) ◽  
pp. 451-467 ◽  
Author(s):  
Marco Henneböhle ◽  
Pierre-Yves Le Roy ◽  
Matthias Hein ◽  
Rudolf Ehrler ◽  
Volker Jäger

AbstractA new approach to optically active N-methylamino acids is presented, relying on stereoselective reduction of N-methylisoxazolinium salts with a dioxyethyl side-chain. The diastereoselectivity of the reduction step is studied systematically, in comparison with that of respective isoxazolines. A two-step transformation of isoxazolinium salts - with NaBH3(OAc) and subsequent catalytic hydrogenation as well as a one-pot reduction by catalytic hydrogenation led to high (95:5 and 87:13) diastereomeric ratios of protected erythro-N-methylaminopentanetriols. The hydroxyethyl side-chain is elaborated by oxidation to afford the β -N-methylamino acid 37, exemplifying the potential of this strategy.


2003 ◽  
Vol 68 (15) ◽  
pp. 5819-5825 ◽  
Author(s):  
Ahmed M. Hafez ◽  
Travis Dudding ◽  
Ty R. Wagerle ◽  
Meha H. Shah ◽  
Andrew E. Taggi ◽  
...  

Author(s):  
Isabelle Gillaizeau ◽  
Yoshinori Tokairin ◽  
Hiroyuki Konno ◽  
Angéline Noireau ◽  
Caroline West ◽  
...  

A new approach for the asymmetric synthesis of the two enantiomers of β-phosphorus-containing α-amino acids was developed via Michael addition of secondary phosphine oxides and dialkyl phosphites to chiral Ni...


1974 ◽  
Vol 22 (11) ◽  
pp. 2614-2623 ◽  
Author(s):  
HIROSHI AKIMOTO ◽  
KYUYA OKAMURA ◽  
MINORU YUI ◽  
TAKAYUKI SHIOIRI ◽  
MASASHI KURAMOTO ◽  
...  

1997 ◽  
Vol 38 (29) ◽  
pp. 5135-5138 ◽  
Author(s):  
Yinglin Han ◽  
Subo Liao ◽  
Wei Qiu ◽  
Chaozhong Cai ◽  
Victor J. Hruby

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Pablo Mier ◽  
Miguel A. Andrade-Navarro

Abstract According to the amino acid composition of natural proteins, it could be expected that all possible sequences of three or four amino acids will occur at least once in large protein datasets purely by chance. However, in some species or cellular context, specific short amino acid motifs are missing due to unknown reasons. We describe these as Avoided Motifs, short amino acid combinations missing from biological sequences. Here we identify 209 human and 154 bacterial Avoided Motifs of length four amino acids, and discuss their possible functionality according to their presence in other species. Furthermore, we determine two Avoided Motifs of length three amino acids in human proteins specifically located in the cytoplasm, and two more in secreted proteins. Our results support the hypothesis that the characterization of Avoided Motifs in particular contexts can provide us with information about functional motifs, pointing to a new approach in the use of molecular sequences for the discovery of protein function.


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