A highly efficient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-DMT]

Balducci, Daniele; Contaldi, Simone; Lazzari, Ilaria; Porzi, Gianni

doi:10.1016/j.tetasy.2009.06.004

Cited by 23 publications

(11 citation statements)

References 19 publications

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“…As discussed above, those building blocks are important tools to explore the topographical preferences of bioactive peptides. The only limits to the systematic exploration of the topographical requirements upon other bioactive peptides are their excessive cost or synthesis that require expensive chiral catalysts . Our methodology, can be used to prepare a wide range of this type of residues, using a variety of commercial or synthetic aldehydes as described in the text, the synthesis provided DMP and DMT and their protected derivatives.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Constrained Unnatural Aromatic Amino Acidsvia Unsaturated Diketopiperazine Intermediate

Mollica

Costante

Mirzaie

et al. 2015

Journal of Heterocyclic Chem

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Unnatural aromatic amino acids are useful tools in drug discovery, since their insertion in bioactive peptide sequences can change the side chains spatial orientation, the backbone conformation and above all, their bioactivity. In this communication, we propose a straightforward method to synthesize 2′,6′‐dimethyl‐tyrosine and 2′,6′‐dimehylphenyl‐alanine derivatives as handling building blocks for peptide synthesis via unsaturated diketopiperazine (DKP) intermediate.

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Section: Resultsmentioning

confidence: 99%

Preparation of Constrained Unnatural Aromatic Amino Acidsvia Unsaturated Diketopiperazine Intermediate

Mollica

Costante

Mirzaie

et al. 2015

Journal of Heterocyclic Chem

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“…JECREO: According to Clemente (2003), the structure as published contains a non-space group translation (case 5) and should be described in P2 1 , Z 0 = 1 instead of P2 1 , Z 0 = 2. There are five more examples of overlooked translations in our set of structures: FAMYUP (Maity et al, 2012), GUHTAF (Balducci et al, 2009), LEPMEZ03 (Schmidt & Jansen, 2012), MOVWIE (Nassimbeni et al, 2009) and RUGDON (Ukrainets et al, 2008). For all of these, the energy minimizations converge to structures in which all atoms without exception match the additional translation within 0.01 Å (see Fig.…”

Section: Two Hundred Reinterpreted Structuresmentioning

confidence: 96%

Validation of missed space-group symmetry in X-ray powder diffraction structures with dispersion-corrected density functional theory

Hempler

Schmidt

Streek

2017

Acta Crystallogr B Struct Sci Cryst Eng Mater

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More than 600 molecular crystal structures with correct, incorrect and uncertain space-group symmetry were energy-minimized with dispersion-corrected density functional theory (DFT-D, PBE-D3). For the purpose of determining the correct space-group symmetry the required tolerance on the atomic coordinates of all non-H atoms is established to be 0.2 Å. For 98.5% of 200 molecular crystal structures published with missed symmetry, the correct space group is identified; there are no false positives. Very small, very symmetrical molecules can end up in artificially high space groups upon energy minimization, although this is easily detected through visual inspection. If the space group of a crystal structure determined from powder diffraction data is ambiguous, energy minimization with DFT-D provides a fast and reliable method to select the correct space group.

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“…During a recent development program we were required to prepare a significant quantity of ( S )- N -Boc-2,6-dimethyltyrosine 1 , and, in order to meet the project timelines, rapid delivery of material was critical. Several routes to this amino acid have been published; however, most have only been run on moderate scale. We selected the asymmetric hydrogenation route shown in Scheme for further investigation as it had been previously demonstrated on kilogram scale. , In this process, the key step is an enantioselective hydrogenation of methyl ( Z )-2-acetamido-3-(4-acetoxy-2,6-dimethylphenyl)-prop-2-enoate 6 with the chiral catalyst, [Rh(1,5-COD)( R , R -DIPAMP)]BF 4 under relatively forcing conditions (60 °C, 60 psi) and high catalyst loading (1 mol %).…”

Section: Introductionmentioning

confidence: 99%

Development of an Asymmetric Hydrogenation Route to (S)-N-Boc-2,6-dimethyltyrosine

Praquin

Koning

Peach

et al. 2011

Org. Process Res. Dev.

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An improved, simpler and potentially more economical route to (S)-N-Boc-2,6-dimethyltyrosine 1, based on a previously published route, is presented. Key modifications were to prepare the dehydroaminoacid hydrogenation substrate 6 in a one-pot process directly from serine methyl ester and 4-iodo-3,5-dimethylphenyl acetate 4 and to identify a significantly more active asymmetric hydrogenation catalyst that allowed a 5-fold reduction in catalyst loading.

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A highly efficient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-DMT]

Cited by 23 publications

References 19 publications

Preparation of Constrained Unnatural Aromatic Amino Acidsvia Unsaturated Diketopiperazine Intermediate

Preparation of Constrained Unnatural Aromatic Amino Acidsvia Unsaturated Diketopiperazine Intermediate

Validation of missed space-group symmetry in X-ray powder diffraction structures with dispersion-corrected density functional theory

Development of an Asymmetric Hydrogenation Route to (S)-N-Boc-2,6-dimethyltyrosine

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