TY - JOUR

T1 - A practical large-scale synthesis of cyclic RGD pentapeptides suitable for further functionalization through click' chemistry

AU - Paleček, Jiří

AU - Dräger, Gerald

AU - Kirschning, Andreas

PY - 2011

Y1 - 2011

N2 - A multigram batch of the cyclo[Arg-Gly-Asp-d-Phe-Lys] and its N - azido derivative was accomplished via solution-phase synthesis using an epimerization-free fragment condensation. The C-terminus of d-Phe was protected as its tert-butyl ester. Fmoc (Arg, Gly, Asp, d-Phe) and Boc (Lys) groups were used to protect all N - termini. The Ts and NO2 groups, respectively were chosen to protect the guanidine group. The macrocyclization step (between d-Phe and l-Lys) was carried out under TBTU/HOBt or DPPA condensation conditions. Finally, the -amino group of the lysine residue was selectively converted into the azido group by a diazo-transfer reaction.

AB - A multigram batch of the cyclo[Arg-Gly-Asp-d-Phe-Lys] and its N - azido derivative was accomplished via solution-phase synthesis using an epimerization-free fragment condensation. The C-terminus of d-Phe was protected as its tert-butyl ester. Fmoc (Arg, Gly, Asp, d-Phe) and Boc (Lys) groups were used to protect all N - termini. The Ts and NO2 groups, respectively were chosen to protect the guanidine group. The macrocyclization step (between d-Phe and l-Lys) was carried out under TBTU/HOBt or DPPA condensation conditions. Finally, the -amino group of the lysine residue was selectively converted into the azido group by a diazo-transfer reaction.

KW - amino acids

KW - cyclizations

KW - diazo compounds

KW - RGD-peptides

KW - solution-phase synthesis

UR - http://www.scopus.com/inward/record.url?scp=79651473089&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1258396

DO - 10.1055/s-0030-1258396

M3 - Article

AN - SCOPUS:79651473089

SP - 653

EP - 661

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 4

M1 - Z28210SS

ER -