ChemInform Abstract: Recent Advances in Stereoselective Synthesis and Application of β-Amino Acids

ChemInform ◽  
2010 ◽  
Vol 41 (12) ◽  
Author(s):  
Brad E. Sleebs ◽  
T. T. Van Nguyen ◽  
Andrew B. Hughes
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Recent Advances

Recent Advances in Stereoselective Synthesis and Application of β-Amino Acids

2009 ◽  
Vol 41 (6) ◽  
pp. 429-478 ◽  
Author(s):  
Brad E. Sleebs ◽  
T. T. Van Nguyen ◽  
Andrew B. Hughes
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Recent Advances

Recent advances in the stereoselective synthesis of β-amino acids

Tetrahedron ◽  
2002 ◽  
Vol 58 (40) ◽  
pp. 7991-8035 ◽  
Author(s):  
Mei Liu ◽  
Mukund P. Sibi
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Recent Advances

Progress in recent development of stereoselective synthesis of β2-amino acid derivatives from β-nitroacrylate derivatives

2020 ◽  
Vol 18 (16) ◽  
pp. 2991-3006
Author(s):  
Hao-Wei Zeng ◽  
Ping-Yu Wu ◽  
Hsyueh-Liang Wu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Stereoselective Synthesis ◽  
Amino Acid Derivatives ◽  
Recent Advances

β2-Amino acids: recent advances in the synthesis of β2-amino acids and their derivatives from various stereoselective transformations of β-nitroacrylates are summarized.

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

scholarly journals Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C–H Functionalization

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5270
Author(s):  
Zhenbo Yuan ◽  
Xuanzhong Liu ◽  
Changmei Liu ◽  
Yan Zhang ◽  
Yijian Rao
Keyword(s):  
Amino Acids ◽  
Direct Synthesis ◽  
Environmentally Friendly ◽  
Powerful Method ◽  
Rapid Synthesis ◽  
Conservation Of Energy ◽  
Mild Conditions ◽  
Recent Advances ◽  
Recent Developments

Non-proteinogenic amino acids have attracted tremendous interest for their essential applications in the realm of biology and chemistry. Recently, rising C–H functionalization has been considered an alternative powerful method for the direct synthesis of non-proteinogenic amino acids. Meanwhile, photochemistry has become popular for its predominant advantages of mild conditions and conservation of energy. Therefore, C–H functionalization and photochemistry have been merged to synthesize diverse non-proteinogenic amino acids in a mild and environmentally friendly way. In this review, the recent developments in the photo-mediated C–H functionalization of proteinogenic amino acids derivatives for the rapid synthesis of versatile non-proteinogenic amino acids are presented. Moreover, postulated mechanisms are also described wherever needed.

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