918667-14-8Relevant articles and documents
Fluorinated Pseudopeptide Analogues of the Neuropeptide 26RFa: Synthesis, Biological, and Structural Studies
Pierry, Camille,Couve-Bonnaire, Samuel,Guilhaudis, Laure,Neveu, Cindy,Marotte, Amelie,Lefranc, Benjamin,Cahard, Dominique,Segalas-Milazzo, Isabelle,Leprince, Jerome,Pannecoucke, Xavier
, p. 1620 - 1633 (2013/09/23)
A series of four fluorinated dipeptide analogues each containing a fluoro-olefin moiety as peptide bond surrogate has been designed and synthesized. These motifs have been successfully introduced into the bioactive C-terminal heptapeptide of the neuropeptide 26RFa by conventional SPPS. We then evaluated the ability of the generated pseudopeptides to increase [Ca2+]i in GPR103-transfected cells. For these fluorinated analogues, greater stability in human serum was observed. Their conformations were also investigated, leading to the valuable identification of differences depending on the position of the fluoro-olefin moiety in the sequence.
Diethylzinc-mediated one-step stereoselective synthesis of α-fluoroacrylates from aldehydes and ketones. Two different pathways depending on the carbonyl partner
Lemonnier,Zoute,Dupas,Quirion,Jubault
experimental part, p. 4124 - 4131 (2009/09/25)
(Chemical Equation Presented) A efficient methodology allowing the one-pot stereoselective synthesis of R-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is descri
Tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly dipeptide isostere
Sano, Shigeki,Kuroda, Yoko,Saito, Katsuyuki,Ose, Yukiko,Nagao, Yoshimitsu
, p. 11881 - 11890 (2007/10/03)
(Z)-α-Fluoro-α,β-unsaturated esters (Z)-7a-f were stereoselectively prepared by a tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates 6a-f with NaBH4 in EtOH. A concise synthesis of Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly (26) as a dipeptide isostere was achieved via the tandem reduction-olefination of the corresponding 2-acyl-2-fluoro-2-phosphonoacetate 20.
