2011
DOI: 10.1002/anie.201106406
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Fine‐tuning the π–π Aromatic Interactions in Peptides: Somatostatin Analogues Containing Mesityl Alanine

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Cited by 21 publications
(21 citation statements)
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“…Moreover, some of these new 14-residue peptides showed high conformational stability (particularly those that also had a D-Trp in position 8), thereby allowing the determination of their 3D structures by NMR for the first time, in a similar way as previous studies devoted to short-ring analogs, including Octreotide. These structures confirmed the relevance of non-covalent interactions between aromatic residues in positions 6, 7 and 11 in the modulation of the conformation and binding behavior of the correspondent Somatostatin analogs222324.…”
supporting
confidence: 70%
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“…Moreover, some of these new 14-residue peptides showed high conformational stability (particularly those that also had a D-Trp in position 8), thereby allowing the determination of their 3D structures by NMR for the first time, in a similar way as previous studies devoted to short-ring analogs, including Octreotide. These structures confirmed the relevance of non-covalent interactions between aromatic residues in positions 6, 7 and 11 in the modulation of the conformation and binding behavior of the correspondent Somatostatin analogs222324.…”
supporting
confidence: 70%
“…Indeed, the aromatic ring of Phe7 has contacts with the Hβ2 of Asn5 and with the Qγ2 methyl groups of Thr10 and Thr12. Consequently, the conformations of peptide 1 are more restricted than the counterpart without the fluorine substitution (D-Trp8-SRIF) previously analyzed22. The binding profile of peptide 1 showed strong affinity to SSTR2, similar to that of Octreotide, and remarkable affinity to SSTR3, in the same order as Somatostatin.…”
Section: Resultsmentioning
confidence: 93%
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