Details
| Original language | English |
|---|---|
| Article number | Z28210SS |
| Pages (from-to) | 653-661 |
| Number of pages | 9 |
| Journal | Synthesis |
| Issue number | 4 |
| Publication status | Published - 2011 |
Abstract
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.
Keywords
- amino acids, cyclizations, diazo compounds, RGD-peptides, solution-phase synthesis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Synthesis, No. 4, Z28210SS, 2011, p. 653-661.
Research output: Contribution to journal › Article › Research › peer review
}
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 -