scholarly journals Efficient Synthesis of β2-Amino Acid by Homologation of α-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile.

ChemInform ◽  
2006 ◽  
Vol 37 (37) ◽  
Author(s):  
Roba Moumne ◽  
Solange Lavielle ◽  
Philippe Karoyan
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Reformatsky Reaction ◽  
Efficient Synthesis ◽  
The Reformatsky Reaction

The use of the reformatsky reaction for the synthesis of β-amino acids

1982 ◽  
Vol 231 (3) ◽  
pp. 185-189 ◽  
Author(s):  
M. Bellassoued ◽  
R. Arous-Chtara ◽  
M. Gaudemar
Keyword(s):  
Amino Acids ◽  
Reformatsky Reaction ◽  
The Reformatsky Reaction

scholarly journals Efficient Synthesis of Peptides with 4-Methylpiperidine as Fmoc Removal Reagent by Solid Phase Synthesis

2017 ◽  
Vol 58 (4) ◽  
Author(s):  
Javier Eduardo García Castañeda ◽  
Cristian Francisco Vergel Galeano ◽  
Zuly Jenny Rivera Monroy ◽  
Javier Eduardo Rosas Pérez
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Synthetic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Amino Group ◽  
Efficient Synthesis ◽  
Phase Synthesis

<p>Solid phase peptide synthesis using the Fmoc/<em>t</em>-Bu strategy (SPPS-Fmoc/tBu) is the most widely used methodology for obtaining synthetic peptides. In this paper, we evaluate the viability of using 4-methylpiperidine as a reagent for deprotection of the amino acid alpha amino group in SPPS-Fmoc/tBu. For this purpose, the peptide (RRWQWRMKKLG) was simultaneously synthesized using 4-methylpiperidine or piperidine for Fmoc removal reagent. The obtained products had similar purities and yields. Finally, 21 peptides were synthesized using 4-methylpiperidine. Our results suggest that is possible to obtain synthetic peptides efficiently by the strategy SPPS-Fmoc/tBu when 4-methylpiperidine was used as reagent to remove Fmoc groups N-alpha protected amino acids.</p>

scholarly journals Efficient Synthesis of New Fluorinated β-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5990
Author(s):  
Sayeh Shahmohammadi ◽  
Ferenc Fülöp ◽  
Enikő Forró
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Ester Hydrochloride ◽  
Enzymatic Method ◽  
Efficient Synthesis ◽  
Preparative Scale ◽  
Carboxylic Ester ◽  
Amino Acid Enantiomers ◽  
Amino Esters ◽  
Hydrolysis Of

An efficient and novel enzymatic method has been developed for the synthesis of β-fluorophenyl-substituted β-amino acid enantiomers through lipase PSIM (Burkholderia cepasia) catalyzed hydrolysis of racemic β-amino carboxylic ester hydrochloride salts 3a–e in iPr2O at 45 °C in the presence of Et3N and H2O. Adequate analytical methods were developed for the enantio-separation of racemic β-amino carboxylic ester hydrochlorides 3a–e and β-amino acids 2a–e. Preparative-scale resolutions furnished unreacted amino esters (R)-4a–e and product amino acids (S)-5a–e with excellent ee values (≥99%) and good chemical yields (>48%).

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