Synthesis of peptides with aziridine-2,3-dicarboxylic acid as an β-amino acid equivalent building block

2006 ◽  
pp. 634-636
Author(s):  
Tanja Schirmeister
Keyword(s):  
Amino Acid ◽  
Dicarboxylic Acid ◽  
Building Block

Quantitative helix handedness bias through a single H vs. CH3 stereochemical differentiation

2021 ◽  
Author(s):  
Daniel Bindl ◽  
Elisabeth Heinemann ◽  
Pradeep Kumar Mandal ◽  
Ivan Huc
Keyword(s):  
Amino Acid ◽  
Building Block

A novel chiral aromatic δ-amino acid building block was shown to fully induce handedness in quinoline oligoamide foldamers with the possibility to further increase the bias by combining multiple of...

scholarly journals Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

2017 ◽  
Vol 13 ◽  
pp. 2153-2156 ◽  
Author(s):  
Shital Kumar Chattopadhyay ◽  
Suman Sil ◽  
Jyoti Prasad Mukherjee
Keyword(s):  
Amino Acid ◽  
Histone Deacetylase ◽  
Building Block ◽  
Suberic Acid ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Important Amino Acid ◽  
New Synthesis ◽  
Cyclic Tetrapeptides ◽  
Derivatives Of

A new synthesis of the important amino acid 2-aminosuberic acid from aspartic acid is reported. The methodology involves the alternate preparation of (S)-2-aminohept-6-enoate ester as a building block and its diversification through a cross-metathesis reaction to prepare the title compounds. The utility of the protocol is demonstrated through the preparation of three suberic acid derivatives of relevance to the design and the synthesis of peptides of biological relevance.

scholarly journals Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary

2016 ◽  
Vol 81 (9) ◽  
pp. 3961-3966 ◽  
Author(s):  
Adrien Vincent ◽  
Damien Deschamps ◽  
Thomas Martzel ◽  
Jean-François Lohier ◽  
Christopher J. Richards ◽  
...  
Keyword(s):  
Amino Acid ◽  
Building Block ◽  
Chiral Auxiliary ◽  
Enantiomerically Pure

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

scholarly journals Regiodivergent Biocatalytic Hydroxylation of L-Glutamine Facilitated by Characterization of Non-Heme Dioxygenases from Non-Ribosomal Peptide Biosyntheses

2021 ◽  
Author(s):  
Hans Renata ◽  
Emily Shimizu ◽  
Christian Zwick
Keyword(s):  
Amino Acid ◽  
Building Block ◽  
Solid Phase ◽  
Functional Characterization ◽  
Free Standing ◽  
Substrate Specificities ◽  
Total Turnover

We report the functional characterization of two iron- and a-ketoglutarate-dependent dioxygenases that are capable of hydroxylating free-standing glutamine at its C3 and C4 position respectively. In particular, the C4 hydroxylase, Q4Ox, catalyzes the reaction with approximately 4,300 total turnover numbers, facilitating synthesis of a solid-phase compatible building block and stereochemical elucidation at the C4 position of the hydroxylated product. This work will enable the development of novel synthetic strategies to prepare useful glutamine derivatives and stimulate further discoveries of new amino acid hydroxylases with distinct substrate specificities.<br>

scholarly journals Regiodivergent Biocatalytic Hydroxylation of L-Glutamine Facilitated by Characterization of Non-Heme Dioxygenases from Non-Ribosomal Peptide Biosyntheses

2021 ◽  
Author(s):  
Hans Renata ◽  
Emily Shimizu ◽  
Christian Zwick
Keyword(s):  
Amino Acid ◽  
Building Block ◽  
Solid Phase ◽  
Functional Characterization ◽  
Free Standing ◽  
Substrate Specificities ◽  
Total Turnover

We report the functional characterization of two iron- and a-ketoglutarate-dependent dioxygenases that are capable of hydroxylating free-standing glutamine at its C3 and C4 position respectively. In particular, the C4 hydroxylase, Q4Ox, catalyzes the reaction with approximately 4,300 total turnover numbers, facilitating synthesis of a solid-phase compatible building block and stereochemical elucidation at the C4 position of the hydroxylated product. This work will enable the development of novel synthetic strategies to prepare useful glutamine derivatives and stimulate further discoveries of new amino acid hydroxylases with distinct substrate specificities.<br>

Synthesis of an Isotopically-labelled Antarctic Fish Antifreeze Glycoprotein Probe

2011 ◽  
Vol 64 (6) ◽  
pp. 723 ◽  
Author(s):  
Joanna M. Wojnar ◽  
Clive W. Evans ◽  
Arthur L. DeVries ◽  
Margaret A. Brimble
Keyword(s):  
Mass Spectrometry ◽  
Amino Acid ◽  
Building Block ◽  
Exocrine Pancreas ◽  
Antarctic Fish ◽  
Antifreeze Glycoproteins ◽  
Threonine Residue ◽  
Antarctic Fishes ◽  
Antifreeze Glycoprotein ◽  
Acid Unit

Antifreeze glycoproteins (AFGPs) are glycosylated polypeptides produced by Antarctic and Arctic fishes, which allow them to survive in seawater at sub-zero temperatures. An investigation into the postulated enteric uptake of AFGP synthesized in the exocrine pancreas of Antarctic fishes required a custom-prepared AFGP probe that incorporated seven isotopically-labelled Ala residues for detection by mass spectrometry. The AFGPs are composed of a repetitive three amino acid unit (Ala-Ala-Thr), in which the threonine residue is glycosylated with the disaccharide β-d-Gal-(1→3)-α-d-GalNAc. The synthesis of isotopically-labelled AFGP8 (1), as well as the optimized synthesis of the protected glycosylated amino acid building block 2, is reported.

Renewable Cyclobutane-1,3-dicarboxylic Acid (CBDA) Building Block Synthesized from Furfural via Photocyclization

2020 ◽  
Vol 8 (24) ◽  
pp. 8909-8917 ◽  
Author(s):  
Zhihan Wang ◽  
Mark Scheuring ◽  
Micah Mabin ◽  
Rahul Shahni ◽  
Zijun D. Wang ◽  
...  
Keyword(s):  
Dicarboxylic Acid ◽  
Building Block

scholarly journals A Reliable Enantioselective Route to Mono-Protected N1-Cbz Piperazic Acid Building Block

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5939
Author(s):  
Evanthia Papadaki ◽  
Dimitris Georgiadis ◽  
Michail Tsakos
Keyword(s):  
Natural Products ◽  
Amino Acid ◽  
Total Synthesis ◽  
Building Block ◽  
Optical Purity ◽  
Protecting Group ◽  
High Optical Purity

The chiral N1-Cbz, N2-H derivative of the piperazic acid monomer is a valuable building block in the total synthesis of natural products, comprising this nonproteinogenic amino acid. In that context, we wish to report an improved synthetic protocol for the synthesis of both (3R)- and (3S)-piperazic acids bearing the carboxybenzyl protecting group (Cbz) selectively at the N1 position. Our method builds on previously reported protocols, circumventing their potential shortcomings, and optimizing the ultimate selective deprotection at the N2 position, thus, offering an efficient and reproducible pathway to suitably modified piperazates in high optical purity.

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