236404-46-9Relevant articles and documents
Non-proteinogenic amino acids in the pThr-2 position of a pentamer peptide that confer high binding affinity for the polo box domain (PBD) of polo-like kinase 1 (Plk1)
Qian, Wen-Jian,Park, Jung-Eun,Lee, Kyung S.,Burke Jr., Terrence R.
supporting information, p. 7306 - 7308 (2013/02/22)
We report herein that incorporating long-chain alkylphenyl-containing non-proteinogenic amino acids in place of His at the pT-2 position of the parent polo-like kinase 1 (Plk1) polo box domain (PBD)-binding pentapeptide, PLHSpT (1a) increases affinity. Fo
Novel synthesis of cyclic amide-linked analogues of angiotensins II and III
Matsoukas,Hondrelis,Agelis,Barlos,Gatos,Ganter,Moore,Moore
, p. 2958 - 2969 (2007/10/02)
Cyclic amide-linked angiotensin II (ANGII) analogues have been synthesized by novel strategies, in an attempt to test the ring clustering and the charge relay bioactive conformation recently suggested. These analogues were synthesized by connecting side chain amino and carboxyl groups at positions 1 and 8, 2 and 8, 3 and 8, and 3 and 5, N-terminal amino and C-terminal carboxyl groups at positions 1 and 8, 2 and 8, and 4 and 8, and side chain amino to C-terminal carboxyl group at positions 1 and 8. All these analogues were biologically inactive, except for cyclic [Sar1,Asp3,Lys5]ANGII (analogue 10) which had high contractile activity in the rat uterus assay (30% of ANGII) and [Lys1,Tyr(Me)4,Glu8]ANGII (analogue 7) which had weak antagonist activity (PA2 ? 6). Precyclic linear peptides synthesized using 2-chlorotrityl chloride resin and N(α)-Fmoc-amino acids with suitable side chain protection were obtained in high yield and purity and were readily cyclized with benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate as coupling reagent. Molecular modeling suggests that the ring structure of the potent analogue can be accommodated in the charge relay conformation proposed for ANGII.