The effect of N-methylation of amino acids (Ac-X-OMe) on solubility and conformation: a DFT study

2015 ◽  
Vol 13 (39) ◽  
pp. 9993-10006 ◽  
Author(s):  
Shah Md. Abdur Rauf ◽  
Per I. Arvidsson ◽  
Fernando Albericio ◽  
Thavendran Govender ◽  
Glenn E. M. Maguire ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Energy Barrier ◽  
Aqueous Solubility ◽  
Conformational Energy ◽  
Dft Study ◽  
Amino Acid Derivatives

N-Methylation of amino acid derivatives (Ac-X-OMe, X = Gly, Val, Leu, Ile, Phe, Met, Cys, Ser, Asp and His) leads to an increase in aqueous solubility, lipophilicity and lowering of the cis/trans amide conformational energy barrier (EA).

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.

Synthesis of New β-Amino Acids via 5-Oxazolidinones and the Arndt - Eistert Procedure

2005 ◽  
Vol 58 (11) ◽  
pp. 778 ◽  
Author(s):  
Andrew B. Hughes ◽  
Brad E. Sleebs
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Reductive Cleavage ◽  
High Yield ◽  
Amino Acid Derivatives ◽  
Peptide Therapeutics

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl α-amino acid, which was then homologated via an Arndt–Eistert procedure in high yield to give the N-methyl β-amino acid.

Chiral sensors for determining the absolute configurations of α-amino acid derivatives

2018 ◽  
Vol 16 (37) ◽  
pp. 8311-8317 ◽  
Author(s):  
Zhongxiang Chen ◽  
Hongjun Fan ◽  
Shiwei Yang ◽  
Guangling Bian ◽  
Ling Song
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
H Nmr ◽  
The Absolute

Two simple 1H NMR tests give the absolute configurations of α-amino acids.

A DFT study on the recognition of α-amino acid derivatives by chiral uranyl–salen

2015 ◽  
Vol 1068 ◽  
pp. 8-12 ◽  
Author(s):  
Giuseppe Forte ◽  
Giuseppe Trusso Sfrazzetto ◽  
Andrea Pappalardo
Keyword(s):  
Amino Acid ◽  
Dft Study ◽  
Amino Acid Derivatives

scholarly journals Nitrosation and analysis of amino acid derivatives by isocratic HPLC

RSC Advances ◽  
2016 ◽  
Vol 6 (16) ◽  
pp. 13120-13128 ◽  
Author(s):  
Songül Ulusoy ◽  
Halil Ibrahim Ulusoy ◽  
Daniel Pleissner ◽  
Niels Thomas Eriksen
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Acid Concentration ◽  
Amino Acid Concentration ◽  
Amino Acid Derivatives ◽  
Hydroxy Acids ◽  
Isocratic Hplc

Amino acids are transformed by nitrosation with dinitrogen trioxide into their corresponding α-hydroxy acids, which are separated and analysed by HPLC, and used to quantify the original amino acid concentration in samples.

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