174653-61-3Relevant academic research and scientific papers
Synthesis of caged peptides using caged lysine: Application to the synthesis of caged AIP, a highly specific inhibitor of calmodulin-dependent protein kinase II
Tatsu, Yoshiro,Shigeri, Yasushi,Ishida, Atsuhiko,Kameshita, Isamu,Fujisawa, Hitoshi,Yumoto, Noboru
, p. 1093 - 1096 (1999)
N(α)-Fmoc-N(ε)-(2-nitrobenzyloxycarbonyl)-lysine has been prepared and used in the solid-phase synthesis of caged peptides. The synthesized caged AIP (cagedKcageKALRRQEAVDAL) showed characteristics required for caged peptides including a significantly red
A Lasso-Inspired Bicyclic Peptide: Synthesis, Structure and Properties
Martin-Gómez, Helena,Albericio, Fernando,Tulla-Puche, Judit
supporting information, p. 19250 - 19257 (2018/12/11)
The chemical synthesis of a bicycle inspired by the natural lasso peptide sungsanpin using a combination of solid-phase and in-solution chemistries is described. The bicyclic-derived topoisomer was designed by introducing a covalent linkage between the ri
Solid-phase synthesis of peptide conjugates derived from the antimicrobial cyclic decapeptide BPC194
Vil, Slvia,Badosa, Esther,Montesinos, Emilio,Feliu, Lidia,Planas, Marta
, p. 1117 - 1129 (2015/02/19)
The solid-phase conjugation of the antimicrobial peptide c(KKLKKFKKLQ) (BPC194) to a linear or cyclic sequence through a 1,2,3-triazole ring is described. Cyclic alkynylpeptidyl resins derived from BPC194 were treated with azidopeptides derived from the antimicrobial peptide BP100 or from the bacteriocin iturin A. The cyclic alkynyl-peptidyl resins incorporated at the 3-position a propargylglycine, a glutamic acid residue derivatized with propargylamine or a lysine bearing a propioloyl group. The reactions of the cyclic alkynyl resins with the BP100-derived azidopeptides depended on the length and the sequence of the azidopeptides. The reactions were performed by treatment of the alkynyl resin with CuI and ascorbic acid, and required the presence of piperidine/DMF or DIEA in 2,6-lutidine/DMF. The latter conditions also allowed the conjugation of the alkynyl-peptidyl resin bearing a propioloyl lysine to a linear or cyclic azidopeptide derived from the cyclic moiety of iturin A.
Solid-phase synthesis of cyclic lipopeptidotriazoles
Vila, Silvia,Camo, Cristina,Figueras, Eduard,Badosa, Esther,Montesinos, Emilio,Planas, Marta,Feliu, Lidia
, p. 4785 - 4794 (2014/08/05)
The solid-phase synthesis of cyclic lipopeptidotriazoles derived from the cyclic decapeptide c(Lys-Lys2-Leu-Lys-Lys5-Phe-Lys-Lys- Leu-Gln) (BPC194), incorporating a triazolyl ring at Lys2 and a hexanoyl group at Lys5, was studied. Four different strategies that required the use of five orthogonal protecting groups (Fmoc, tBu, All, pNZ, ivDde) were explored. The influence of the side-chain protection of Lys 2 and Lys5 with the ivDde and pNZ groups was evaluated by incorporating Lys2(ivDde)/Lys5(pNZ) or Lys 2(pNZ)/Lys5(ivDde). The order of removal of these protecting groups and of the introduction of the hexanoyl and triazolyl moieties was also studied. The best strategy included: (i) synthesis of a cyclic peptidyl resin bearing Lys2(ivDde) and Lys5(pNZ); (ii) pNZ group removal; (iii) acylation with hexanoic acid; (iv) ivDde group removal; and (v) acylation with propiolic acid followed by an azide-alkyne 1,3-dipolar cycloaddition. By using this protocol, a set of cyclic lipopeptidotriazoles was prepared in high purities.
