81184-10-3Relevant academic research and scientific papers
Environmentally benign peptide synthesis using liquid-assisted ball-milling: Application to the synthesis of Leu-enkephalin
Bonnamour, Julien,Metro, Thomas-Xavier,Martinez, Jean,Lamaty, Frederic
, p. 1116 - 1120 (2013/06/05)
This paper describes an original methodology for peptide bond synthesis avoiding toxic solvents and reactants. Ball-milling stoichiometric amounts of Boc-protected α-amino acid N-carboxyanhydrides (Boc-AA-NCA) or Boc-protected α-amino acid N-hydroxysuccin
N-Hydroxy Amides. Part 5. Synthesis and Properties of N-Hydroxypeptides having Leucine Enkephalin Sequences
Akiyama, Masayasu,Iesaki, Katsuhito,Katoh, Akira,Shimizu, Kazuyuki
, p. 851 - 856 (2007/10/02)
In order to study the effects of the N-hydroxy amide group, N-hydroxyenkephalin analogues with the H-Tyr-(OH)X-Gly-Phe-Leu-OH sequence, where X=Gly, L-Ala, or β-Ala, have been synthesized.A (1)H n.m.r. study indicates that the N-hydroxyenkephalins have a type I β-turn structure in dimethyl sulphoxide solution.From the interaction of (HO)Gly- and β-(HO)Ala-analogues with Cu(II) it is suggested that the hydroxyamide function exerts a definite influence on the complexation.These N-hydroxyenkephalins are resistant to aminopeptidase M.A qualitative analgesia test shows that the (HO)Ala-analogue possesses a more lasting potency than that of Leu5-enkephalin, while having a comparable activity.
N-Hydroxy Amides. III. Active Esters of Polystyrene-bound 1-Hydroxy-2-pyrrolidinone and Their Use in Peptide Synthesis
Akiyama, Masayasu,Shimizu, Kazuyuki,Aiba, Seiichi,Katoh, Hiroaki
, p. 1421 - 1425 (2007/10/02)
A polymer-bond cyclic N-hydroxy amide has been prepared by reaction of aminomethylated copoly(styrene-2percent divinylbenzene) with 1-hydroxy-5-oxo-3-pyrrolidinecarboxylic acid using dicyclohexylcarbodiimide (DCC) as a condensing agent.Several N-blocked α-amino acids have been loaded on this resin by use of DCC.The amino acid resin can be utilized for peptide synthesis.Repetitive usage of the resin in the form of esters and facile synthesis of a biologically active pentapeptide, Leu5-enkephalin, show the usefulness of the polymer-bound 1-hydroxy-2-pyrrolidinone.
Studies on Amino Acids and Peptides. Part 6. Methods for Introducing Thioamide Bonds into the Peptide Backbone: Synthesis of the Four Monothio Analogues of Leucine Enkephalin
Clausen, Kim,Thorsen, Michael,Lawesson, Sven-Olov,Spatola, Arno F.
, p. 785 - 798 (2007/10/02)
A methodology for preparing peptide analogues in which a thioamide bond replaces the normal amide bond is described.Thus, the synthesis of the three leucine enkephalin analogues 4>-, 2>-, and 1>-leucine enke
