ChemInform Abstract: Synthesis of (S)-N-tert-Butoxycarbonyl-N,O-isopropylidene-α-methylserinal: A Potential Building Block for the Asymmetric Synthesis of Non-Natural Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 30 (14) ◽  
pp. no-no
Author(s):  
Myriam Alias ◽  
Carlos Cativiela ◽  
Maria D. Diaz-de-Villegas ◽  
Jose A. Galvez ◽  
Yolanda Lapena
Tetrahedron ◽  
1998 ◽  
Vol 54 (49) ◽  
pp. 14963-14974 ◽  
Author(s):  
Myriam Alías ◽  
Carlos Cativiela ◽  
María D. Díaz-de-Villegas ◽  
JoséA. Gálvez ◽  
Yolanda Lapeña

Author(s):  
Liuzhu Wang ◽  
Shiqing Diao ◽  
Yangyang Sun ◽  
Shuiqin Jiang ◽  
Yan Liu ◽  
...  

L-Homoalanine, a useful building block for the synthesis of several chiral drugs, is generally synthesized through biocascades using natural amino acids as cheap starting reactants. However, the addition of expensive...


2020 ◽  
Author(s):  
Shubin Liu

Homochirality is a common feature of amino acids and carbohydrates, whose origin is still unknown. For example, 19 of 20 natural amino acids are L-chiral but deoxyribose sugars in DNA are always D-chiral. Meanwhile, right-handed helices are ubiquitous in nature. Are these two phenomena intrinsically correlated? Here, we propose that homochirality of amino acids and nucleotide sugars is originated from the handedness of helices. We show that right-handed 3<sub>10-</sub>helix and alpha-helix favor the L-chiral form for amino acids, but for deoxyribose sugars right-handed helices prefer the D-chiral form instead. Our analyses unveil that there exist strong cooperativity effects dominated by electrostatic interactions. This work not only resolves the mystery of homochirality by providing a unified explanation for the origin of homochirality in proteins and DNA using helical secondary structures as the root cause, but also ratifies the Principle of Chirality Hierarchy, where chirality of a higher hierarchy dictates that of lower ones. Possible applications of the present work to asymmetric synthesis and macromolecular assembly are discussed.


2003 ◽  
Vol 682 (1-2) ◽  
pp. 143-148 ◽  
Author(s):  
Károly Micskei ◽  
Orsolya Holczknecht ◽  
Csongor Hajdu ◽  
Tamás Patonay ◽  
Valér Marchis ◽  
...  

2020 ◽  
Vol 07 ◽  
Author(s):  
Kantharaju Kamanna

: This review highlights the application of biopolymers of natural α-amino acids and its derived wild type peptides employed as an organocatalysis for the asymmetric synthesis published by researchers across the globe is described. The α-amino acids with L-stereochemistry are available commercial in pure form are played crucial role in enantioselective chiral molecule synthesis. Out of twenty natural amino acids, only one secondary amine containing proline amino acid exhibited revolution in the field of orgnocatalysis, because of its rigid structure and formation of an imine like transition state during the reaction lead more stereoselectivity. Hence, it is referred to as a simple enzyme in organocatalyst. Further discussed chiral organic molecule synthesis by employing oligopeptides derived from the natural amino acids as a robust biocatalyst replaced enzyme catalysts. The peptide includes di-, tri, tetra-, penta- and oligopeptide derived demonstrated as a potential organocatalysts, whose reaction activity and mechanistic pathways are reviewed. Several choice of families of these organocatalysts permit chemist to achieve facile and efficient stereoselective synthesis of many complex natural products with optically pure isomer. Subsequently, researcher developed green and sustainable heterogeneous catalytic system containing organocatalyst immobilized onto solid inorganic supports or porous materials, and is responsible for accelerating the reaction through heterogeneous phase. The developed heterogeneous organocatalysts-MOFs found to be used easier and employed for bulk production and flow reactor synthesis. This review compiled many outstanding discoveries in organocatalysts derived amino acids and it’s heterogenized on to MOFs together role of the organocatalysis in many organic transformations in academic and industrial applications are covered.


2020 ◽  
Author(s):  
Shubin Liu

Homochirality is a common feature of amino acids and carbohydrates, whose origin is still unknown. For example, 19 of 20 natural amino acids are L-chiral but deoxyribose sugars in DNA are always D-chiral. Meanwhile, right-handed helices are ubiquitous in nature. Are these two phenomena intrinsically correlated? Here, we propose that homochirality of amino acids and nucleotide sugars is originated from the handedness of helices. We show that right-handed 3<sub>10-</sub>helix and alpha-helix favor the L-chiral form for amino acids, but for deoxyribose sugars right-handed helices prefer the D-chiral form instead. Our analyses unveil that there exist strong cooperativity effects dominated by electrostatic interactions. This work not only resolves the mystery of homochirality by providing a unified explanation for the origin of homochirality in proteins and DNA using helical secondary structures as the root cause, but also ratifies the Principle of Chirality Hierarchy, where chirality of a higher hierarchy dictates that of lower ones. Possible applications of the present work to asymmetric synthesis and macromolecular assembly are discussed.


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