5[Kpsi(CH2N)PR]-TASP, HB-19

Chemical Name: N2,N6-[H-L-Lys[psi(CH2N)]L-Pro-L-Arg]-L-Lys-L-Lys-N6-[H-L-Lys[psi(CH2N)]L-Pro-L-Arg]-L-Lys-Gly-L-Pro-N6-[H-L-Lys[psi(CH2N)]L-Pro-L-Arg]-L-Lys-L-Glu-N6-[H-L-Lys[psi(CH2N)]L-Pro-L-Arg]-L-Lys-Gly-L-Cys-OH; N2,N6-Bis[1-[(2S)-2,6-diaminohexyl]-L-prolyl-L-arginyl]-L-lysyl-L-lysyl-N6-[1-[(2S)-2,6-diaminohexyl]-L-prolyl-L-arginyl]-L-lysylglycyl-L-prolyl-N6-[1-[(2S)-2,6-diaminohexyl]-L-prolyl-L-arginyl]-L-lysyl-L-alpha-glutamyl-N6-[1-[(2S)-2,6-diaminohexyl]-L-prolyl-L-arginyl]-L-lysylglycyl-L-cysteine
CAS No. 175297-53-7
项目整合开发状态: Preclinical
项目研究机构: CNRS (Originator), Institut Pasteur (Originator)
合成路线:The title compound was obtained by solid-phase peptide synthesis starting from N-Boc-S-(4-methylbenzyl)cysteine linked to PAM resin (I).The protected peptide template (XVII) was synthesized by sequential coupling-deprotection cycles using the appropriate combination of either Boc- or Fmoc- N-alpha-protected amino acids.The following side-chain-protected amino acid residues were assembled: Gly (III),Lys(Boc) (V),Glu(cyclohexyl ester) (VII),Lys(Boc) (V),Pro (X),Gly (III),Lys(Boc) (V),Lys(chlorobenzyloxycarbonyl) (XIV) and Lys(Boc) (XVI) to produce the peptide resins (IV),(VI),(VIII),(IX),(XI),(XII),(XIII),(XV) and (XVII),respectively.Subsequent removal of the N-terminal and the four side-chain Boc protecting groups by means of trifluoroacetic acid yielded the peptide resin (XVIII).

合成路线:Simultaneous coupling of five N-Boc-arginin (XIX) residues to the free amino groups of the peptide template (XVIII),followed by acid deprotection of the Boc groups,furnished (XX).To this were assembled five N-Boc-proline residues (XXI) to provide,after acid deprotection,resin (XXII).Then,reductive condensation with Boc-protected lysinal (XXIII) furnished the protected pseudopeptide adduct (XXIV).Finally,simultaneous cleavage from the resin and removal of protecting groups was effected by treatment with anhydrous hydrogen fluoride.