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4 article(s) from Budisa, Nediljko

Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

Vladimir Kubyshkin,
Rebecca Davis and
Nediljko Budisa

Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40

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Figure 1: The structures of the fluoroprolines discussed herein.

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Figure 2: The distinction between “the alanine and the proline worlds”. While the polyalanine backbone leads ...

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Figure 3: Molecular volume for 20 coded amino acids and fluoroprolines. The COSMO volume was calculated for a...

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Figure 4: Comparative analysis of the electrostatic potential for proline and fluoroprolines (electrostatic p...

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Figure 5: Experimental logP data for methyl esters of N-acetylamino acids.

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Figure 6: The conformational dependence of the proline ring on the fluorination at position 4.

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Figure 7: Rotation around the peptidyl-prolyl fragments in polypeptide structures is important for correct ov...

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Figure 8: The complex fate of a protein-encoded amino acid in the cell (EF-Tu – elongation factor thermo unst...

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Figure 9: Metabolic routes for proline in E. coli. A) Synthesis of proline and B) degradation of proline.

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Figure 10: A complete flowchart for the proline incorporation into proteins during ribosomal biosynthesis. A) ...

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Figure 11: Amide bond formation capacities of fluoroprolines compared to some coded amino acids measured on ri...

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Figure 12: Ribbon representation of the X-ray crystal structures of proteins containing fluoroprolines. A) Enh...

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Figure 13: Problems and phenomena associated with the production of a protein-containing proline-to-fluoroprol...

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Figure 14: Effects of fluoroprolines on recombinant protein expression using the auxotrophic expression host E...

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Figure 15: A) Experimental setup for the incorporation of fluoroprolines into proteins. B) Adaptive laboratory...

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Published 15 Feb 2021

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Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models

Vladimir Kubyshkin and
Nediljko Budisa

Beilstein J. Org. Chem. 2017, 13, 2442–2457, doi:10.3762/bjoc.13.241

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Figure 1: A. Dependence of the lipophilicity (logP) on the number of fluorine atoms in a partially fluorinate...

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Scheme 1: Synthesis of the model compounds.

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Figure 2: Kinetics of the C-terminal ester hydrolysis.

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Figure 3: Partitioning of the esters 1–5 between octan-1-ol and water. Insert: comparison with the other part...

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Scheme 2: Amide isomerism in the N-acetylprolyl fragment.

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Figure 4: Enhancement of the trans/cis thermodynamic preferences in the ester models as a function of the sol...

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Scheme 3: A. Four-state conformational equilibrium model used by Siebler et al. [72] for explanations of the elev...

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Scheme 4: Elevation of the trans/cis ratio in derivatives of N-acyl proline may result from the enhanced n→π*...

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Scheme 5: Synthesis of the model peptides.

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Figure 5: Mean residue molar circular dichroism (Δε) of peptides 8–10 in methanol (left) and aqueous phosphat...

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Figure 6: Conformational analysis of the peptides by ¹H DOSY NMR (D₂O, 298 K). The theoretical values were ca...

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Figure 7: Hydrolysis of the C-terminal 2,2-difluoroethyl esters of the oligopeptides in buffered deuterium ox...

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Published 16 Nov 2017

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cis–trans-Amide isomerism of the 3,4-dehydroproline residue, the ‘unpuckered’ proline

Vladimir Kubyshkin and
Nediljko Budisa

Beilstein J. Org. Chem. 2016, 12, 589–593, doi:10.3762/bjoc.12.57

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Scheme 1: s-cis–s-trans Amide bond isomerism in an N-acyl-proline fragment.

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Figure 1: Amino acids that have been compared in this study.

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Figure 2: X-ray crystal structures of compounds 5–9. Carbon- grey, nitrogen – blue, oxygen – red, fluorine – ...

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Scheme 2: The relationship between the pK_a of the ammonium function in the amino acid and the amide rotationa...

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Figure 3: The double bond between C³ and C⁴ atoms in 3,4-dehydroproline residues induces an increase in the a...

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Published 29 Mar 2016

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Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

Michaela Mühlberg,
Michael G. Hoesl,
Christian Kuehne,
Jens Dernedde,
Nediljko Budisa and
Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

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Scheme 1: Protein design and dual-functionalization of TTL: periodate cleavage, oxime ligation and CuAAC.

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Figure 1: Dual-functionalization of TTL: A) MALDI–MS spectra (red: modified protein (as marked below); black:...

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Figure 2: SPR measurements: A) set-up showing different binding events of the double-functionalized TTL to EC...

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Published 13 May 2015

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