64410-79-3Relevant academic research and scientific papers
New aspects of β-lactam chemistry: β-lactams as chiral building blocks
Ojima, Iwao,Shimizu, Nobuko,Qiu, Xiaogang,Chen, Hauh-Jyun C.,Nakahashi, Kazuaki
, p. 649 - 658 (2007/10/02)
Recent advances on the new aspects of β-lactam chemistry in which β-lactams are used as chiral building blocks for the synthesis of a variety of α-amino acids, 4α-alkyl-α-aminoacids, oligopeptides, labeled peptides, azetidines, amino alcohols, etc., are reviewed.The topics include new and effective routes to dipeptides via homochiral β-lactams obtained by extremely stereoselective cycloadditions of chiral ketenes to chiral imines, a novel route to labeled peptides through extremely stereoselective and stereospecific reductive cleavage of β-lactams on a palladium catalyst, and new efficient syntheses of α-alkyl-α-amino acids and their peptides by the highly effective asymmetric alkylations of β-lactam lithium enolates followed by hydrogenolysis or Birch reduction.Mechanism of those highly selective unique reactions are discussed.
SYNTHESIS OF OPTICALLY PURE ENKEPHALIN ANALOG, ENKEPHALIN, USING CHIRAL β-LACTAMS AS SYNTHETIC INTERMEDIATES
Hatanaka, Naoto,Abe, Rumiko,Ojima, Iwao
, p. 445 - 448 (2007/10/02)
Optically pure pentapeptide, L-Tyr-D-Ala-Gly-L-Phe-L-Leu-ol (1) wich is an analog of opioid hormone. enkephalin, was succesfully synthesized by using β-lactam building blocks as synthons of peptide units.
