Trifluoroacetic acid-mediated intramolecular formal N-H insertion reactions with amino-α-diazoketones: a facile and efficient synthesis of optically pure pyrrolidinones and piperidinones

2000 ◽  
Vol 78 (6) ◽  
pp. 800-808 ◽  
Author(s):  
Hua Yang ◽  
Valdas Jurkauskas ◽  
Nicole Mackintosh ◽  
Tobias Mogren ◽  
Corey RJ Stephenson ◽  
...  
Keyword(s):  
Amino Acid ◽  
Trifluoroacetic Acid ◽  
Efficient Synthesis ◽  
Insertion Reactions ◽  
C And N ◽  
Optically Pure

Trifluoroacetic acid (TFA) was found to promote intramolecular formal N-H insertion reactions. Upon treatment with TFA, optically pure N-Boc-β'-amino-α-diazoketones (5a-c) and N-Boc-γ'-amino-α-diazoketones (10a-d) can be converted, with retention of chirality, into pyrrolidinones (11a-c) and piperidinones (12a-d), respectively, with concomitant removal of the Boc group, in good to excellent yields.Key words: α-diazoketone, amino acid, pyrrolidinone, piperidinone, N-H insertion.

scholarly journals Translational Selection and Yeast Proteome Evolution

Genetics ◽  
2003 ◽  
Vol 164 (4) ◽  
pp. 1291-1303 ◽  
Author(s):  
Hiroshi Akashi
Keyword(s):  
Natural Selection ◽  
Amino Acid ◽  
Amino Acid Composition ◽  
Acid Composition ◽  
Synonymous Codon ◽  
Amino Acid Usage ◽  
Proper Function ◽  
Efficient Synthesis ◽  
Expression Levels ◽  
Speed And Accuracy

AbstractThe primary structures of peptides may be adapted for efficient synthesis as well as proper function. Here, the Saccharomyces cerevisiae genome sequence, DNA microarray expression data, tRNA gene numbers, and functional categorizations of proteins are employed to determine whether the amino acid composition of peptides reflects natural selection to optimize the speed and accuracy of translation. Strong relationships between synonymous codon usage bias and estimates of transcript abundance suggest that DNA array data serve as adequate predictors of translation rates. Amino acid usage also shows striking relationships with expression levels. Stronger correlations between tRNA concentrations and amino acid abundances among highly expressed proteins than among less abundant proteins support adaptation of both tRNA abundances and amino acid usage to enhance the speed and accuracy of protein synthesis. Natural selection for efficient synthesis appears to also favor shorter proteins as a function of their expression levels. Comparisons restricted to proteins within functional classes are employed to control for differences in amino acid composition and protein size that reflect differences in the functional requirements of proteins expressed at different levels.

Highly Stereoselective Synthesis of Optically Pure C-Aryl Imines from α-L-Amino Acid Methyl Esters.

ChemInform ◽  
2004 ◽  
Vol 35 (17) ◽  
Author(s):  
Antonella Leggio ◽  
Adolfo Le Pera ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
Claudio Romeo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Stereoselective Synthesis ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

ChemInform Abstract: Efficient Synthesis of Modular Amino Acid Derivatives Containing Selenium with Pronounced GPx-Like Activity.

ChemInform ◽  
2010 ◽  
Vol 41 (3) ◽  
Author(s):  
Eduardo E. Alberto ◽  
Letiere C. Soares ◽  
Jessie H. Sudati ◽  
Antonio C. A. Borges ◽  
Joao B. T. Rocha ◽  
...  
Keyword(s):  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Efficient Synthesis

scholarly journals An Efficient Synthesis of Novel Adamantane β-Amino Acid: 2-(Adamant-2-yl)-3-aminopropanoic Acid

2012 ◽  
Vol 85 (4) ◽  
pp. 419-423 ◽  
Author(s):  
Vesna Petrović Peroković ◽  
Rosana Ribić ◽  
Biserka Prugovečki ◽  
Dubravka Matković-Čalogović ◽  
Srđanka Tomić
Keyword(s):  
Amino Acid ◽  
Efficient Synthesis

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

Two-step chiral transfer from d-penicillamine to metallosupramolecular ionic crystals

2018 ◽  
Vol 54 (39) ◽  
pp. 5003-5006 ◽  
Author(s):  
Yuhei Yasukawa ◽  
Nobuto Yoshinari ◽  
Takumi Konno
Keyword(s):  
Amino Acid ◽  
Ionic Crystals ◽  
Optically Pure

Optically pure ionic crystals composed of complex cations and anions are created from a racemic complex and an amino acid.

scholarly journals Tandem four-component reaction for efficient synthesis of dihydrothiophene with substituted amino acid ethyl esters

RSC Advances ◽  
2018 ◽  
Vol 8 (40) ◽  
pp. 22498-22505 ◽  
Author(s):  
Jing Sun ◽  
Yu Zhang ◽  
Chao-Guo Yan
Keyword(s):  
Amino Acid ◽  
Aromatic Aldehydes ◽  
Ethyl Esters ◽  
Efficient Synthesis ◽  
One Pot ◽  
The One

The one-pot four-component reaction of aromatic aldehydes, malononitrile, 1,3-thiazolidinedione and ethyl glycinate hydrochloride in ethanol in the presence of triethylamine afforded trans-dihydrothiophene.

Sign in / Sign up

Export Citation Format

Share Document