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- W4387650701 abstract "The enormous influence in terms of bioactivity, affinity, and selectivity represented by the replacement of (L)-2,6-dimethyl tyrosine (Dmt) instead of Phenylalanine (Phe) into Nociceptin/orphanin (N/OFQ) neuropeptide analogues, has been well documented in literature. More recently, the non-natural amino acid (L)-2-methyl tyrosine (Mmt), with steric hindrance among Tyr and Dmt, has been studied because of the modulation of steric effects in opioid peptide chains. Here we report a new synthetic strategy to obtain Mmt based on the well-known Pd-catalyzed ortho-C(sp2)–H activation approach, since there is a paucity of other synthetic routes in literature, to achieve it. The aim of this work was to force only the mono ortho-methylation process over the double ortho-methylation one. In this regard we are pleased to report that the introduction of the dibenzylamine moiety on Tyr aromatic nucleus is a convenient and traceless solution to achieve such a goal. Interestingly, our method provided the aimed Mmt either as N-Boc or N-Fmoc derivatives ready to be inserted into peptide chains through solid phase peptide synthesis (SPPS). Importantly, the introduction of Mmt in place of Phe1 in the sequence of N/OFQ(1-13)-NH2 was very well tolerated in terms of pharmacological profile and bioactivity." @default.
- W4387650701 created "2023-10-16" @default.
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- W4387650701 date "2023-10-09" @default.
- W4387650701 modified "2023-10-16" @default.
- W4387650701 title "(L)-Mono-methyl Tyrosine (Mmt): new synthetic strategy via bulky ‘forced-traceless’ regioselective Pd-catalyzed C(sp2)–H activation" @default.
- W4387650701 doi "https://doi.org/10.20944/preprints202310.0471.v1" @default.
- W4387650701 hasPublicationYear "2023" @default.
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