scholarly journals Diastereoselective Synthesis of b-Branched a-Amino Acids via Bio-catalytic Dynamic Kinetic Resolution

2021 ◽  
Author(s):  
Fuzhuo Li ◽  
Li-Cheng Yang ◽  
Jingyang Zhang ◽  
Jason Chen ◽  
Hans Renata
Keyword(s):  
Amino Acids ◽  
Total Synthesis ◽  
Kinetic Resolution ◽  
Diastereoselective Synthesis ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process ◽  
Biocatalytic Reaction

We report a biocatalytic transamination method to prepare a broad range of b-branched a-amino acids that proceeds with high diastereo- and enantioselectivity. Mechanistic studies show that the transformation proceeds through a dynamic kinetic resolution process that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction is applied to the synthesis of several cyclic fragments and in the first total synthesis of jomthonic acid A.

scholarly journals Diastereoselective Synthesis of b-Branched a-Amino Acids via Bio-catalytic Dynamic Kinetic Resolution

2021 ◽  
Author(s):  
Fuzhuo Li ◽  
Li-Cheng Yang ◽  
Jingyang Zhang ◽  
Jason Chen ◽  
Hans Renata
Keyword(s):  
Amino Acids ◽  
Total Synthesis ◽  
Kinetic Resolution ◽  
Diastereoselective Synthesis ◽  
Mechanistic Studies ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process ◽  
Biocatalytic Reaction

We report a biocatalytic transamination method to prepare a broad range of b-branched a-amino acids that proceeds with high diastereo- and enantioselectivity. Mechanistic studies show that the transformation proceeds through a dynamic kinetic resolution process that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction is applied to the synthesis of several cyclic fragments and in the first total synthesis of jomthonic acid A.

Stereoselective Synthesis ofanti-β-Hydroxy-α-amino Acids through Dynamic Kinetic Resolution

2004 ◽  
Vol 116 (7) ◽  
pp. 900-902 ◽  
Author(s):  
Kazuishi Makino ◽  
Takayuki Goto ◽  
Yasuhiro Hiroki ◽  
Yasumasa Hamada
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Dynamic Kinetic Resolution

Recyclable Ligands for the Non-Enzymatic Dynamic Kinetic Resolution of Challenging α-Amino Acids

2015 ◽  
Vol 54 (44) ◽  
pp. 12918-12922 ◽  
Author(s):  
Yong Nian ◽  
Jiang Wang ◽  
Shengbin Zhou ◽  
Shuni Wang ◽  
Hiroki Moriwaki ◽  
...  
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution

Enzymatic Dynamic Kinetic Resolution of Oxazinones: A New Approach to Enantiopure β2-Amino Acids

ChemCatChem ◽  
2011 ◽  
Vol 3 (2) ◽  
pp. 319-330 ◽  
Author(s):  
Albrecht Berkessel ◽  
Ilona Jurkiewicz ◽  
Resmi Mohan
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
New Approach

Stereoselective Synthesis ofanti-β-Hydroxy-α-amino Acids through Dynamic Kinetic Resolution

2004 ◽  
Vol 43 (7) ◽  
pp. 882-884 ◽  
Author(s):  
Kazuishi Makino ◽  
Takayuki Goto ◽  
Yasuhiro Hiroki ◽  
Yasumasa Hamada
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Dynamic Kinetic Resolution

scholarly journals New Enzymatic Method of Chiral Amino Acid Synthesis by Dynamic Kinetic Resolution of Amino Acid Amides: Use of Stereoselective Amino Acid Amidases in the Presence of α-Amino-ε-Caprolactam Racemase

2007 ◽  
Vol 73 (16) ◽  
pp. 5370-5373 ◽  
Author(s):  
Shigenori Yamaguchi ◽  
Hidenobu Komeda ◽  
Yasuhisa Asano
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Kinetic Resolution ◽  
Acid Synthesis ◽  
Enzymatic Method ◽  
Ochrobactrum Anthropi ◽  
Dynamic Kinetic Resolution ◽  
Amino Acid Synthesis

ABSTRACT d- and l-amino acids were produced from l- and d-amino acid amides by d-aminopeptidase from Ochrobactrum anthropi C1-38 and l-amino acid amidase from Pseudomonas azotoformans IAM 1603, respectively, in the presence of α-amino-ε-caprolactam racemase from Achromobacter obae as the catalyst by dynamic kinetic resolution of amino acid amides.

scholarly journals Asymmetric total synthesis of rotenoids via organocatalyzed dynamic kinetic resolution

2019 ◽  
Vol 2 (1) ◽  
Author(s):  
Saima Perveen ◽  
Shuang Yang ◽  
Miao Meng ◽  
Weici Xu ◽  
Guoxiang Zhang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Dynamic Kinetic Resolution ◽  
Asymmetric Total Synthesis

Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic­ Substitution at Phosphorus Center

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4922-4932
Author(s):  
Piotr Borowski ◽  
Marek Stankevič ◽  
Dorota Strzelecka ◽  
Olga Bąk
Keyword(s):  
Organophosphorus Compound ◽  
Kinetic Resolution ◽  
Phosphinic Acid ◽  
Predominant Formation ◽  
Chiral Alcohols ◽  
Chiral Alcohol ◽  
Dynamic Kinetic Resolution ◽  
Resolution Process

Reaction of racemic phosphinic acid derivatives with chiral alcohols proceeds with predominant formation of one diastereomer. The highest level of enrichment has been obtained for transesterfication of racemic methyl benzylphenylphosphinate (64% de). The outcome of the reaction depends on both the structure of chiral alcohol and the starting organophosphorus compound. The results strongly suggest that the nature of the observed phenomena is not a classical equilibration of intermediates found in dynamic kinetic resolution process but is a result of a different reactivity of both enantiomers of racemic substrate towards the same chiral nucleophile.

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