An efficient synthesis of a novel analog of octreotide with an unnatural l-lysine-like tetrazolyl amino acid |
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Authors: | Elena A Popova Sofia K NikolskaiaIvan A Gluzdikov Rostislav E Trifonov |
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Institution: | Saint-Petersburg State University, Institute of Chemistry, Universitetskii pr. 26, Peterhof, Saint-Petersburg 198504, Russia |
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Abstract: | A new cyclic octreotide-like octapeptide was prepared by incorporation of an unnatural tetrazolyl amino acid, an analog of Fmoc-l-lysine, into the peptide chain. The new tetrazolyl amino acid, (S)-2-{2-(9H-fluoren-9-yl)acetoxy]amino}-6-(1H-tetrazol-1-yl)hexanoic acid, was obtained by azidation of Fmoc-l-lysine trifluoroacetate with sodium azide in the presence of triethyl orthoformate in glacial acetic acid. The linear peptide sequence was prepared using efficient Fmoc/t-Bu solid-phase peptide synthesis (SPPS). Cyclization of the octapeptide was carried out via oxidation with iodine. The structure and purity of the cyclic octapeptide were confirmed by LC–MS, MALDI-TOF MS/MS analysis as well as 1D/2D 1H and 13C NMR spectroscopy. |
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Keywords: | XUAURGHUNZKOHJ-DXAXHBCISA-N KSSNYHFBDHCJLF-FQEVSTJZSA-N |
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