Memory of Chirality of Tertiary Aromatic Amides: A Simple and Efficient Method for the Enantioselective Synthesis of Quaternary α-Amino Acids

2009 ◽  
Vol 131 (30) ◽  
pp. 10711-10718 ◽  
Author(s):  
Mathieu Branca ◽  
Sébastien Pena ◽  
Régis Guillot ◽  
Didier Gori ◽  
Valérie Alezra ◽  
...  
Keyword(s):  
Amino Acids ◽  
Efficient Method ◽  
Enantioselective Synthesis ◽  
Memory Of Chirality

Memory of Chirality in the Enantioselective Synthesis of β-Lactams Derived from Amino Acids. Influence of the Reaction Conditions.

ChemInform ◽  
2003 ◽  
Vol 34 (41) ◽  
Author(s):  
M. Angeles Bonache ◽  
Guillermo Gerona-Navarro ◽  
Mercedes Martin-Martinez ◽  
M. Teresa Garcia-Lopez ◽  
Pilar Lopez ◽  
...  
Keyword(s):  
Amino Acids ◽  
Enantioselective Synthesis ◽  
Reaction Conditions ◽  
Memory Of Chirality

Memory of Chirality in a Flow-Based System: Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors

2018 ◽  
Vol 2018 (47) ◽  
pp. 6754-6757 ◽  
Author(s):  
Antonin Mambrini ◽  
Didier Gori ◽  
Cyrille Kouklovsky ◽  
Heejin Kim ◽  
Jun-ichi Yoshida ◽  
...  
Keyword(s):  
Amino Acids ◽  
Enantioselective Synthesis ◽  
Memory Of Chirality ◽  
Flow Microreactors

scholarly journals Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids, Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes

2021 ◽  
Author(s):  
Eryn Nelson ◽  
Jeffrey S. S. K. Formen ◽  
Christian Wolf
Keyword(s):  
Amino Acids ◽  
Absolute Configuration ◽  
Rapid Determination ◽  
Amino Alcohols ◽  
Enantioselective Synthesis ◽  
Widespread Occurrence ◽  
Chiral Compounds ◽  
New Methods ◽  
The Absolute

The widespread occurrence and significance of chiral compounds does not only require new methods for their enantioselective synthesis but also efficient tools that allow rapid determination of the absolute configuration,...

scholarly journals An Efficient Method for the Reduction of N-Protected Amino Acids and Peptides to the Corresponding Alcohols

1999 ◽  
Vol 23 (7) ◽  
pp. 424-425
Author(s):  
T. Naqvi ◽  
M. Bhattacharya ◽  
W. Haq
Keyword(s):  
Amino Acids ◽  
Efficient Method

Reduction of pentachlorophenyl esters of Boc protected amino acids and peptides to the corresponding alcohols is described.

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

A facile one pot route for the synthesis of imide tethered peptidomimetics

2016 ◽  
Vol 14 (2) ◽  
pp. 556-563 ◽  
Author(s):  
Veladi Panduranga ◽  
Girish Prabhu ◽  
Roopesh Kumar ◽  
Basavaprabhu Basavaprabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
One Pot ◽  
Protected Amino Acid

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

An Efficient Method for the Reduction of N-Protected Amino Acids and Peptides to the Corresponding Alcohols

1999 ◽  
pp. 424-425 ◽  
Author(s):  
T. Naqvi ◽  
M. Bhattacharya ◽  
W. Haq
Keyword(s):  
Amino Acids ◽  
Efficient Method

Chiral azo compounds: enantioselective synthesis and transformations into β-amino alcohols and α-amino acids with a quaternary stereocenter

2011 ◽  
Vol 52 (6) ◽  
pp. 655-657 ◽  
Author(s):  
Friedrich R. Dietz ◽  
Agnes Prechter ◽  
Harald Gröger ◽  
Markus R. Heinrich
Keyword(s):  
Amino Acids ◽  
Amino Alcohols ◽  
Enantioselective Synthesis ◽  
Azo Compounds ◽  
Quaternary Stereocenter
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