A unified approach to mesityl amino acids based on Sharpless dihydroxylation

Ramón, Rosario; Alonso, Mònica; Riéra, Antoni

doi:10.1016/j.tetasy.2007.10.041

Cited by 11 publications

(5 citation statements)

References 24 publications

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“…Finally, the replacement of all three phenylalanine residues with Msa afforded peptide 10 . Fmoc-L-3-mesitylalanine was obtained either following the procedure previously developed by our group [42] or by enantioselective hydrogenation [43,44].…”

Section: Introductionmentioning

confidence: 99%

Insights into Structure-Activity Relationships of Somatostatin Analogs Containing Mesitylalanine

et al. 2013

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Received : 30 October 2013; in revised form: 12 November 2013 / Accepted: 13 November 2013 / Published: 25 November 2013 Abstract: The non-natural amino acid mesitylalanine (2,4,6-trimethyl-L-phenylalanine; Msa) has an electron-richer and a more conformationally restricted side-chain than that of its natural phenylalanine counterpart. Taking these properties into account, we have synthesized ten somatostatin analogs containing Msa residues in different key positions to modify the intrinsic conformational flexibility of the natural hormone. We have measured the binding affinity of these analogs and correlated it with the main conformations they OPEN ACCESSMolecules 2013, 18 14565 populate in solution. NMR and computational analysis revealed that analogs containing one Msa residue were conformationally more restricted than somatostatin under similar experimental conditions. Furthermore, we were able to characterize the presence of a hairpin at the pharmacophore region and a non-covalent interaction between aromatic residues 6 and 11. In all cases, the inclusion of a D-Trp in the eighth position further stabilized the main conformation. Some of these peptides bound selectively to one or two somatostatin receptors with similar or even higher affinity than the natural hormone. However, we also found that multiple incorporations of Msa residues increased the life span of the peptides in serum but with a loss of conformational rigidity and binding affinity.

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Section: Introductionmentioning

confidence: 99%

Insights into Structure-Activity Relationships of Somatostatin Analogs Containing Mesitylalanine

et al. 2013

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“…[19] The four peptides containing Msa, at either position 6 [l-Msa6, (4), and [l-Msa7]-SRIF (5), were prepared by solid-phase peptide synthesis on 2-chlorotrityl chloride resin, using the Fmoc/tBu strategy. Scheme 1 shows the preparation of [l-Msa6,d-Trp8]-SRIF (2).…”

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Fine‐tuning the π–π Aromatic Interactions in Peptides: Somatostatin Analogues Containing Mesityl Alanine

et al. 2011

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“… a Reagents and conditions: (a) see ref ; (b) ClTs (1.02 equiv), NEt 3 (1.5 equiv), CH 2 Cl 2 , 0 °C, 70 h; (c) K 2 CO 3 (3 equiv), H 2 O (5 equiv), DMF, rt, 24 h. …”

Section: Resultsmentioning

confidence: 99%

Phosphinite Thioethers Derived from Chiral Epoxides. Modular P,S-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions

Caldentey

Pericàs

2010

J. Org. Chem.

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A new family of modular P,S-ligands has been prepared from enantiopure arylglycidols. These ligands have been iteratively optimized with respect to four different structural parameters for use in Pd-catalyzed allylic substitutions. As a final output, highly active and enantioselective ligands for these synthetically important transformations have been developed, and the factors controlling their catalytic behavior have been rationalized. From a methodological point of view, a convenient procedure for the regioselective ring-opening of cis-glycidic esters with bulky thiols to yield the corresponding beta-alkylthio-alpha-hydroxy carboxylic acids has been developed.

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A unified approach to mesityl amino acids based on Sharpless dihydroxylation

Cited by 11 publications

References 24 publications

Insights into Structure-Activity Relationships of Somatostatin Analogs Containing Mesitylalanine

Insights into Structure-Activity Relationships of Somatostatin Analogs Containing Mesitylalanine

Fine‐tuning the π–π Aromatic Interactions in Peptides: Somatostatin Analogues Containing Mesityl Alanine

Phosphinite Thioethers Derived from Chiral Epoxides. Modular P,S-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions

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