Stereoselective Synthesis of (2S,3R)-α-Hydroxy-β-Amino Acids (AHBAs): Valinoctin A, (2S,3R)-3-Amino-2-Hydroxydecanoic Acid, and a Fluorescent-Labeled (2S,3R)-AHBA

2014 ◽  
Vol 79 (22) ◽  
pp. 11215-11225 ◽  
Author(s):  
Sharad Chandrakant Deshmukh ◽  
Pinaki Talukdar
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis

scholarly journals Peculiarities of promiscuous l-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids

2021 ◽  
Author(s):  
Shan Wang ◽  
Hai Deng
Keyword(s):  
Amino Acids ◽  
Organic Molecules ◽  
Stereoselective Synthesis ◽  
Enantioselective Synthesis ◽  
General Mechanism ◽  
Future Developments ◽  
Key Points ◽  
Biomaterial Science ◽  
One Step ◽  
Harsh Conditions

Abstract The introduction of β-hydroxy-α-amino acids (βHAAs) into organic molecules has received considerable attention as these molecules have often found widespread applications in bioorganic chemistry, medicinal chemistry and biomaterial science. Despite innovation of asymmetric synthesis of βHAAs, stereoselective synthesis to control the two chiral centres at Cα and Cβ positions is still challenging, with poor atomic economy and multi protection and deprotection steps. These syntheses are often operated under harsh conditions. Therefore, a biotransformation approach using biocatalysts is needed to selectively introduce these two chiral centres into structurally diverse molecules. Yet, there are few ways that enable one-step synthesis of βHAAs. One is to extend the substrate scope of the existing enzyme inventory. Threonine aldolases have been explored to produce βHAAs. However, the enzymes have poor controlled installation at Cβ position, often resulting in a mixture of diastereoisomers which are difficult to be separated. In this respect, l-threonine transaldolases (LTTAs) offer an excellent potential as the enzymes often provide controlled stereochemistry at Cα and Cβ positions. Another is to mine LTTA homologues and engineer the enzymes using directed evolution with the aim of finding engineered biocatalysts to accept broad substrates with enhanced conversion and stereoselectivity. Here, we review the development of LTTAs that incorporate various aldehyde acceptors to generate structurally diverse βHAAs and highlight areas for future developments. Key points • The general mechanism of the transaldolation reaction catalysed by LTTAs • Recent advances in LTTAs from different biosynthetic pathways • Applications of LTTAs as biocatalysts for production of βHAAs

Stereoselective Synthesis of b‐Branched Aromatic a‐Amino Acids via Biocatalytic Dynamic Kinetic Resolution

2021 ◽  
Author(s):  
Fuzhuo Li ◽  
Li-Cheng Yang ◽  
Jingyang Zhang ◽  
Jason Chen ◽  
Hans Renata
Keyword(s):  
Amino Acids ◽  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Dynamic Kinetic Resolution

Stereoselective Synthesis of Chiral β-Fluoro α-Amino Acids via Pd(II)-Catalyzed Fluorination of Unactivated Methylene C(sp3)–H Bonds: Scope and Mechanistic Studies

2015 ◽  
Vol 137 (25) ◽  
pp. 8219-8226 ◽  
Author(s):  
Qi Zhang ◽  
Xue-Song Yin ◽  
Kai Chen ◽  
Shuo-Qing Zhang ◽  
Bing-Feng Shi
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Mechanistic Studies

Stereoselective synthesis of .alpha.-alkyl .alpha.-amino acids. Alkylation of 3-substituted 5H,10bH-oxazolo[3,2-c][1,3]benzoxazine-2(3H),5-diones

1990 ◽  
Vol 55 (20) ◽  
pp. 5437-5439 ◽  
Author(s):  
Thomas M. Zydowsky ◽  
Edwin De Lara ◽  
Stephen G. Spanton
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis

Stereoselective Synthesis of β-Alkylated α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated Methylene C(sp3)–H Bonds with Primary Alkyl Halides

2013 ◽  
Vol 135 (32) ◽  
pp. 12135-12141 ◽  
Author(s):  
Shu-Yu Zhang ◽  
Qiong Li ◽  
Gang He ◽  
William A. Nack ◽  
Gong Chen
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Alkyl Halides ◽  
Palladium Catalyzed

scholarly journals A stereoselective synthesis of α-deuterium-labelled (S)-α-amino acids

Amino Acids ◽  
2010 ◽  
Vol 39 (3) ◽  
pp. 849-858 ◽  
Author(s):  
Elaine O’Reilly ◽  
Daniele Balducci ◽  
Francesca Paradisi
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis

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
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