Enantioselective synthesis of an unnatural bipyridyl amino acid and its incorporation into a peptide

Kise, Kenneth J.; Bowler, Bruce E.

doi:10.1016/s0957-4166(98)00350-4

Cited by 19 publications

(6 citation statements)

References 20 publications

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“…In a recent novel synthetic route for preparing the enantiopure compound, Aspergillus acylase was used for the effective separation of a racemic mixture of N-Ac-7-azatryptophan [101]. In a recent novel synthetic route for preparing the enantiopure compound, Aspergillus acylase was used for the effective separation of a racemic mixture of N-Ac-7-azatryptophan [101].…”

Section: Biosynthetic Approaches To the Production And Resolutionmentioning

confidence: 99%

Recent Advances in the Synthesis of Unnatural α-Amino Acids

Perdih¹,

Dolenc

2007

COC

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The synthesis of unnatural -amino acids is an area of research that has gained a lot of attention in recent years. The availability of synthetic methods for novel unnatural amino acid derivatives and related compounds will be a critical point in the de novo design of molecules that mimic the conformation of the natural, active peptides. These molecules (peptidomimetics) are designed to display high receptor affinity and selectivity, in addition to enhanced bioavailability and metabolic stability.This review focuses on selected recent synthetic methodologies leading to unnatural -amino acids including chiral catalysts that enable enantioselective synthesis and microwave-assisted synthesis. Solid phase synthesis and construction of organometallic amino acids reveal the scope of influence that this field has in organic chemistry. Additionally, the article is aimed to provide a brief insight into the biosynthetic approaches to the synthesis of -amino acid derivatives, and to give the reader an appreciation of the field.

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Section: Biosynthetic Approaches To the Production And Resolutionmentioning

confidence: 99%

Recent Advances in the Synthesis of Unnatural α-Amino Acids

Perdih¹,

Dolenc

2007

COC

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“…Though biology features a heterocycle, His, within its tool‐box, the chelating bpy can be used to form more stable complexes, and allows one to reproduce interesting ‘traditional’ inorganic chemistry complexes. Whilst bpy attachment at position 6 leads to steric hindrance and poor metal binding, when bound in positions 4 or 5, metal binding is readily achieved (Figure 4 d and e) …”

Section: Non‐proteinogenic Amino Acidsmentioning

confidence: 99%

“…[24] Though biology features ah eterocycle, His, within its tool-box, the chelating bpy can be used to form more stable complexes,a nd allows one to reproduce interesting 'traditional' inorganic chemistry complexes.W hilst bpy attachment at position6leads to steric hindrance andp oor metal binding, [25] when bound in positions 4o r5 ,m etal binding is readily achieved (Figure 4d and 4e). [26] Bpy is ac ommon ligand in ruthenium coordination chemistry,a nd Ru II coordination has been used to trigger CC assembly.S imilar to the Ln III induced folding work described in section 2.1 and 3.1, Ghadiri and co-workersw ere the first to report how a1 5r esidue peptidew ith ab py located at its Nterminus coulds pontaneously self-assemble in the presence of Ru II to yield as table three-stranded CC on formation of aR u(bpy) 3 unit. [27] The latter being robust due to the slow ligand exchange kinetics associated with Ru II .…”

Section: Heterocyclic Derivativesmentioning

confidence: 99%

De Novo Design of Xeno‐Metallo Coiled Coils

Slope

Peacock

2015

Chemistry An Asian Journal

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Bioinorganic chemists aspire to achieve the same exquisite and highly controlled inorganic chemistry featured in biology. An exciting mimetic approach involves the use of miniature artificial protein scaffolds designed de novo (often based on the coiled coil (CC) scaffold), for reproducing native metal ion sites and their function. Recently, there is increased interest, instead, in the design of xeno-metal sites within CC assemblies. This involves incorporating either non-biological metal ions, cofactors or non-proteinogenic amino acid ligands for metal ion coordination, whilst retaining a minimal CC protein scaffold. Using this approach, one should be able to create functional designs with unique and unusual properties, which combine the advantages of both biology and 'traditional' non-biological inorganic chemistry. It is the recent progress with respect to the design of xeno-metallo CCs which will be discussed in this Focus Review.

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“…In a few cases, metal ion-assisted self-organizing processes have been described, which lead to peptide assembly into topologically predetermined protein tertiary structures. [5][6][7][8][9][10][11] For example, either bidentate or monodentate ligands, appended to one end of the peptide helix, have been exploited to bring together the helices through coordination to the metallic site, with a metal ion assisted self-organizing molecular process. Similarly, threehelix (Scheme 1a) and four-helix bundles (Scheme 1b) have been reported to be formed in solution through coordination of N-donor ligands (appended to an α-helix C-terminal) to a metal center.…”

Section: Introductionmentioning

confidence: 99%

Conformational and coordination properties of a peptide containing the novel α,α-bis(2-pyridyl)glycine amino acidElectronic supplementary information (ESI) available: Figs. 1S, 2S. See http://www.rsc.org/suppdata/dt/b2/b209199b/

et al. 2003

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A fully protected tripeptide containing a novel C α,α -disubstituted glycine-α,α-di(2-pyridyl)glycine (2Dpy)-in the central position and C α,α -dimethylglycine (Aib) in positions 1 and 3 was synthesized and structurally characterized by single crystal X-ray analysis. The 2Dpy residue bears two 2-pyridyl moieties, which may coordinate metal ions, and promote self-assembly of peptide units. The tripeptide Z-Aib 1 -2Dpy 2 -Aib 3 -OCH 3 (Z: benzyloxycarbonyl) adopts in the solid state a folded type III (IIIЈ) β-turn conformation (with Aib 1 -2Dpy 2 as corner residues), stabilized by an i i ϩ 3 hydrogen bond between the Aib 3 NH and the urethane CO group. The peptide was able to self-assemble in the presence of Cu() ions, giving rise to an octahedral complex with a 2 : 1 peptide/Cu() stoichiometry, which has been structurally characterized. The metal ion, arranged on a crystallographic symmetry centre, is coordinated by two symmetry related 2Dpy residues, which act as tridentate ligands: each 2Dpy residue donates to the Cu() the N atoms of both pyridyl moieties in the equatorial positions, and the carbonyl oxygen atom in the axial positions. A very similar folded conformation characterizes the peptide in both the free and metal-bound states. This indicates that the overall peptide structure is ready to coordinate the metal ion without substantial conformational changes. Metal binding of the tri-peptide toward copper ions was analyzed by UV-visible spectroscopy performed in methanol solution. The experimental data agree with an equilibrium between two species in solution, one in the ratio Cu/ peptide 1 : 1, the other 1 : 2. The formation constants are 9.7 × 10 3 M Ϫ1 and 3.5 × 10 2 M Ϫ1 , respectively. The molar extinction coefficients are 66 ± 3 M Ϫ1 cm Ϫ1 (590 nm) for the 2 : 1 complex and 17 ± 2 M Ϫ1 cm Ϫ1 (690 nm) for the other. All the data obtained in the present work suggest that the 2Dpy residue is well suited to be accommodated into folded conformations. The spontaneous formation of an ordered structure by the 2Dpy containing tri-peptide and copper ions may guide toward the design of more elaborate self-assembling systems. † Electronic supplementary information (ESI) available: Figs. 1S, 2S. See

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Enantioselective synthesis of an unnatural bipyridyl amino acid and its incorporation into a peptide

Cited by 19 publications

References 20 publications

Recent Advances in the Synthesis of Unnatural α-Amino Acids

Recent Advances in the Synthesis of Unnatural α-Amino Acids

De Novo Design of Xeno‐Metallo Coiled Coils

Conformational and coordination properties of a peptide containing the novel α,α-bis(2-pyridyl)glycine amino acidElectronic supplementary information (ESI) available: Figs. 1S, 2S. See http://www.rsc.org/suppdata/dt/b2/b209199b/

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