Towards a streamlined synthesis of peptides containing α,β -dehydroamino acids†

2021 ◽  
pp. 153175
Author(s):  
Diego A. Moyá ◽  
Michael A. Lee ◽  
Joseph C. Chanthakhoun ◽  
Austin K. LeSueur ◽  
Daniel Joaquin ◽  
...  
Keyword(s):  
Dehydroamino Acids

ChemInform Abstract: Stereoselective Synthesis of Dehydroamino Acids Using Malonic Acid Half Oxyester and Aromatic Aldehydes.

ChemInform ◽  
2016 ◽  
Vol 47 (34) ◽  
Author(s):  
Yuttapong Singjunla ◽  
Silvia Colombano ◽  
Jerome Baudoux ◽  
Jacques Rouden
Keyword(s):  
Malonic Acid ◽  
Stereoselective Synthesis ◽  
Aromatic Aldehydes ◽  
Dehydroamino Acids

scholarly journals Deconjugation of Dehydroamino Acids: Stereoselective Synthesis of Racemic (E)-Vinylglycines.

ChemInform ◽  
2006 ◽  
Vol 37 (14) ◽  
Author(s):  
Paul A. Alexander ◽  
Stephen P. Marsden ◽  
Dulce M. Munoz Subtil ◽  
John C. Reader
Keyword(s):  
Stereoselective Synthesis ◽  
Dehydroamino Acids

scholarly journals Conformational properties of N-acetyl-N-methyl-alpha,beta-dehydroalanine N'-methylamide.

2006 ◽  
Vol 53 (1) ◽  
pp. 227-232 ◽  
Author(s):  
Agnieszka Macedowska ◽  
Dawid Siodłak ◽  
Barbara Rzeszotarska
Keyword(s):  
Cyclic Peptides ◽  
Conformational Flexibility ◽  
Biological Action ◽  
Torsion Angles ◽  
Dehydroamino Acids ◽  
Theoretical Methods ◽  
Conformational Properties ◽  
Alpha Beta

The conformational properties of Ac-Delta(Me)Ala-NHMe (N-acetyl-N-methyl-alpha,beta-dehydroalanine N'-methylamide), as the simplest model of N-methyl-alpha,beta-dehydroamino acids, was examined with theoretical methods and in comparison with Ac-DeltaAla-NHMe and Ac-DeltaAla-NMe(2). The N-terminal amide of the Delta(Me)Ala residue easily adopts the configuration cis and the torsion angles phi, psi are highly flexible. The Delta(Me)Ala residue is a conformational flexibilizer as compared to the parent DeltaAla, which is a conformational stiffener. This seems to be the reason why Delta(Me)Ala is found in small natural cyclic peptides, where it ensures the conformational flexibility necessary for biological action.

Synthesis of Peptides with α,β-Dehydroamino Acids, III. Debenzyloxycarbonylation and Detrifluoroacetylation of Dehydroalanine and Dehydrophenylalanine Peptides

1985 ◽  
Vol 1985 (7) ◽  
pp. 1457-1464 ◽  
Author(s):  
Maciej Makowski ◽  
Barbara Rzeszotarska ◽  
Leszek Smelka ◽  
Zbigniew Kubica
Keyword(s):  
Dehydroamino Acids

Synthesis of β-Benzo[b]thiophene Dehydroamino Acids by Suzuki Palladium Catalyzed Cross Coupling

2001 ◽  
pp. 36-37
Author(s):  
Paula M. T. Ferreira ◽  
Hernâni L. S. Maia ◽  
Luís S. Monteiro ◽  
Maria-João R. P. Queiroz ◽  
Natália Silva
Keyword(s):  
Cross Coupling ◽  
Dehydroamino Acids ◽  
Palladium Catalyzed

H8-MonoPhos and its application in catalytic enantioselective hydrogenation of α-dehydroamino acids

Tetrahedron ◽  
2002 ◽  
Vol 58 (43) ◽  
pp. 8799-8803 ◽  
Author(s):  
Qingle Zeng ◽  
Hui Liu ◽  
Aiqiao Mi ◽  
Yaozhong Jiang ◽  
Xingshu Li ◽  
...  
Keyword(s):  
Enantioselective Hydrogenation ◽  
Dehydroamino Acids

A Ring-Closing Metathesis Approach to Cyclic α,β-Dehydroamino Acids

2008 ◽  
Vol 350 (1) ◽  
pp. 95-106 ◽  
Author(s):  
Koen F. W. Hekking ◽  
Dennis C. J. Waalboer ◽  
Marcel A. H. Moelands ◽  
Floris L. van Delft ◽  
Floris P. J. T. Rutjes
Keyword(s):  
Ring Closing Metathesis ◽  
Dehydroamino Acids
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