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An efficient synthesis of a novel analog of octreotide with an unnatural L-lysine-like tetrazolyl amino acid. / Popova, E.A.; Nikolskaia, S.K.; Gluzdikov, I.A.; Trifonov, R.E.

в: Tetrahedron Letters, Том 55, № 36, 2014, стр. 5041-5046.

Результаты исследований: Научные публикации в периодических изданиях › статья

Harvard

Popova, EA, Nikolskaia, SK, Gluzdikov, IA & Trifonov, RE 2014, 'An efficient synthesis of a novel analog of octreotide with an unnatural L-lysine-like tetrazolyl amino acid', Tetrahedron Letters, Том. 55, № 36, стр. 5041-5046. https://doi.org/10.1016/j.tetlet.2014.07.067

APA

Popova, E. A., Nikolskaia, S. K., Gluzdikov, I. A., & Trifonov, R. E. (2014). An efficient synthesis of a novel analog of octreotide with an unnatural L-lysine-like tetrazolyl amino acid. Tetrahedron Letters, 55(36), 5041-5046. https://doi.org/10.1016/j.tetlet.2014.07.067

Vancouver

Popova EA, Nikolskaia SK, Gluzdikov IA, Trifonov RE. An efficient synthesis of a novel analog of octreotide with an unnatural L-lysine-like tetrazolyl amino acid. Tetrahedron Letters. 2014;55(36):5041-5046. https://doi.org/10.1016/j.tetlet.2014.07.067

Author

Popova, E.A. ; Nikolskaia, S.K. ; Gluzdikov, I.A. ; Trifonov, R.E. / An efficient synthesis of a novel analog of octreotide with an unnatural L-lysine-like tetrazolyl amino acid. в: Tetrahedron Letters. 2014 ; Том 55, № 36. стр. 5041-5046.

BibTeX

@article{951dafa8b86e4c2eb648bc6c9d2efa6b,
title = "An efficient synthesis of a novel analog of octreotide with an unnatural L-lysine-like tetrazolyl amino acid",
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.",
keywords = "Unnatural amino acid 1H-Tetrazole L-Lysine Cyclic peptides Somatostatin analogs",
author = "E.A. Popova and S.K. Nikolskaia and I.A. Gluzdikov and R.E. Trifonov",
year = "2014",
doi = "10.1016/j.tetlet.2014.07.067",
language = "English",
volume = "55",
pages = "5041--5046",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "36",

}

RIS

TY - JOUR

T1 - An efficient synthesis of a novel analog of octreotide with an unnatural L-lysine-like tetrazolyl amino acid

AU - Popova, E.A.

AU - Nikolskaia, S.K.

AU - Gluzdikov, I.A.

AU - Trifonov, R.E.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - Unnatural amino acid 1H-Tetrazole L-Lysine Cyclic peptides Somatostatin analogs

U2 - 10.1016/j.tetlet.2014.07.067

DO - 10.1016/j.tetlet.2014.07.067

M3 - Article

VL - 55

SP - 5041

EP - 5046

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 36

ER -

ID: 5710391