caa a22 4500 445326301 CHVBK 20180317142722.0 cr unu---uuuuu 170323e20110301xx s 000 0 eng 10.1007/s10989-010-9238-4 doi (NATIONALLICENCE)springer-10.1007/s10989-010-9238-4 Investigation of the Best Conditions to Obtain c(RGDfK) Peptide on Solid Phase [Elektronische Daten] [Annarita Del Gatto, Mariarosaria De Simone, Ivan de Paola, Michele Saviano, Laura Zaccaro] The cyclic pentapeptide c(RGDfK) is a high affinity ligand of alphaVbeta3 integrin. It was an analog of Cilengitide (EMD 121974) developed to be employed as tracer for cancer diagnosis and therapy by functionalisation of its Lys side-chain. Solution-phase and solid-phase synthetic approaches were previously reported. In the attempt to improve solid-phase synthesis of the cyclopeptide circumventing cyclodimerisation reactions, a systematic study of the synthetic conditions was performed, evaluating and optimising parameters directly involved in the ring closure step. The three-dimensional orthogonal solid-phase strategy developed in this study yields the desired c(RGDfK) peptide with no cyclodimerisation by-products. The protocols described allow the modification of the peptide directly on the solid support in order to obtain novel derivatives for biomedical applications. Springer Science+Business Media, LLC, 2011 Optimisation nationallicence Synthesis nationallicence Reaction nationallicence Pharmaceuticals nationallicence All : Allyl nationallicence tBu : Tert-butyl nationallicence DCM : Dichloromethane nationallicence DIPEA : N,N-diisopropylethylamine nationallicence DMF : N,N-dimethylformamide nationallicence EDT : Ethanedithiol nationallicence f : d-phenylalanine nationallicence LC/ESI/MS : Liquid chromatography electrospray ionisation mass spectrometry nationallicence Fmoc : 9H-fluoren-9-ylmethyloxycarbonyl nationallicence HBTU : 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate nationallicence HOBt : 1-Hydroxybenzotriazole nationallicence ivDde : 1-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-3-methyl-butyl nationallicence MALDI-TOF spectrometry : Matrix-assisted laser desorption ionization time-of-flight mass spectrometry nationallicence MeIm : 1-Methylimidazole nationallicence MSNT : (1-(Mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole) nationallicence Mtt : Methyltrityl nationallicence Pbf : 2,2,4,6,7-Pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl nationallicence PEG : Polyethylene glycol nationallicence PyBop : Benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate nationallicence RP-HPLC : Reverse phase-high performance liquid chromatography nationallicence TFA : Trifluoroacetic acid nationallicence TIS : Triisopropylsilane nationallicence Del Gatto Annarita Istituto di Biostrutture e Bioimmagini—CNR, Via Mezzocannone 16, 80134, Naples, Italy aut De Simone Mariarosaria Dipartimento delle Scienze Biologiche, Università degli Studi di Napoli "Federico II”, Via Mezzocannone 16, 80134, Naples, Italy aut de Paola Ivan Dipartimento delle Scienze Biologiche, Università degli Studi di Napoli "Federico II”, Via Mezzocannone 16, 80134, Naples, Italy aut Saviano Michele Istituto di Cristallografia—CNR, Via Giovanni Amendola 122/O, 70126, Bari, Italy aut Zaccaro Laura Istituto di Biostrutture e Bioimmagini—CNR, Via Mezzocannone 16, 80134, Naples, Italy aut International Journal of Peptide Research and Therapeutics Springer Netherlands 17/1(2011-03-01), 39-45 1573-3149 17:1<39 2011 17 10989 https://doi.org/10.1007/s10989-010-9238-4 text/html Onlinezugriff via DOI 1 brief-communication jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10989-010-9238-4 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Del Gatto Annarita Istituto di Biostrutture e Bioimmagini—CNR, Via Mezzocannone 16, 80134, Naples, Italy aut NATIONALLICENCE 700 1- De Simone Mariarosaria Dipartimento delle Scienze Biologiche, Università degli Studi di Napoli "Federico II”, Via Mezzocannone 16, 80134, Naples, Italy aut NATIONALLICENCE 700 1- de Paola Ivan Dipartimento delle Scienze Biologiche, Università degli Studi di Napoli "Federico II”, Via Mezzocannone 16, 80134, Naples, Italy aut NATIONALLICENCE 700 1- Saviano Michele Istituto di Cristallografia—CNR, Via Giovanni Amendola 122/O, 70126, Bari, Italy aut NATIONALLICENCE 700 1- Zaccaro Laura Istituto di Biostrutture e Bioimmagini—CNR, Via Mezzocannone 16, 80134, Naples, Italy aut NATIONALLICENCE 773 0- International Journal of Peptide Research and Therapeutics Springer Netherlands 17/1(2011-03-01), 39-45 1573-3149 17:1<39 2011 17 10989 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer