Protection of the indole nucleus of tryptophan in solid-phase peptide synthesis with a dipeptide that can be cleaved rapidly at physiological pH
2011 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1873-3581, Vol. 52, no 44, 5876-5879 p.Article in journal (Refereed) Published
The synthesis of a new derivative of tryptophan Fmoc-Trp(Boc-Sar-Sar)-OH is described. Fmoc-Trp(Boc-Sar-Sar)-OH is introduced into peptides by solid-phase peptide synthesis and during treatment with TFA at the end of the synthesis, the Boc group is cleaved and the peptide is obtained with the indole nucleus modified with the sarcosinyl-sarcosinyl (Sar-Sar) moiety. This modification will introduce a cationic charge that improves the solubility of the peptide during HPLC purification. The Sar-Sar moiety is cleaved upon exposure to physiological pH. The Boc-Sar-Sar group might, therefore, also find use in the design of pro-drugs of indole-containing compounds.
Place, publisher, year, edition, pages
2011. Vol. 52, no 44, 5876-5879 p.
Solid-phase peptide synthesis, Protecting group, Cyclization-activated prodrugs, Tryptophan, Fmoc amino acids
Research subject Neurochemistry with Molecular Neurobiology
IdentifiersURN: urn:nbn:se:su:diva-69881DOI: 10.1016/j.tetlet.2011.08.172ISI: 000296168300039OAI: oai:DiVA.org:su-69881DiVA: diva2:479788
authorCount :32012-01-182012-01-152015-03-16Bibliographically approved