Hosahudya N. Gopi

article

Metal‐Coordinated Supramolecular Polymers from the Minimalistic Hybrid Peptide Foldamers

Sanjit Dey, Rajkumar Misra, Abhijith Saseendran, Saikat Pahan, more

Angewandte Chemie International Edition > 60 > 18 > 9863 - 9868

Availing the peptide folded architectures to design metal‐coordinated frameworks and cages is restricted due to the scarcity of readily accessible short and stable secondary structures. The secondary structures, α‐helix and β‐sheets, play significant roles in stabilizing tertiary folds of proteins. Designing such helical structures from the short sequences of peptides without having any steric restrictions...

article

Metal‐Coordinated Supramolecular Polymers from the Minimalistic Hybrid Peptide Foldamers

Sanjit Dey, Rajkumar Misra, Abhijith Saseendran, Saikat Pahan, more

Angewandte Chemie > 133 > 18 > 9951 - 9956

Availing the peptide folded architectures to design metal‐coordinated frameworks and cages is restricted due to the scarcity of readily accessible short and stable secondary structures. The secondary structures, α‐helix and β‐sheets, play significant roles in stabilizing tertiary folds of proteins. Designing such helical structures from the short sequences of peptides without having any steric restrictions...

article

Structural Investigation of Hybrid Peptide Foldamers Composed of α‐Dipeptide Equivalent β‐Oxy‐δ⁵‐amino Acids

Rahi M. Reja, Vivek Kumar, Gijo George, Rajat Patel, more

Chemistry – A European Journal > 26 > 19 > 4304 - 4309

Due to their equivalent lengths, δ‐amino acids can serve as surrogates of α‐dipeptides. However, δ‐amino acids with proteinogenic side chains have not been well studied because of synthetic difficulties and because of their insolubility in organic solvents. Recently we reported the spontaneous supramolecular gelation of δ‐peptides composed of β(O)‐δ⁵‐amino acids. Here, we report the incorporation...

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Metal‐Helix Frameworks from Short Hybrid Peptide Foldamers

Rajkumar Misra, Abhijith Saseendran, Sanjit Dey, Hosahudya N. Gopi

Angewandte Chemie International Edition > 58 > 8 > 2251 - 2255

The potential of structured peptides has not been explored much in the design of metal‐organic frameworks (MOFs). This is partly due to the difficulties in obtaining stable secondary structures from the short α‐peptide sequences. Here we report the design, crystal conformations, coordination site dependent different silver coordinated frameworks of short α,γ‐hybrid peptide 12‐helices consisting of...

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Metal‐Helix Frameworks from Short Hybrid Peptide Foldamers

Rajkumar Misra, Abhijith Saseendran, Sanjit Dey, Hosahudya N. Gopi

Angewandte Chemie > 131 > 8 > 2273 - 2277

The potential of structured peptides has not been explored much in the design of metal‐organic frameworks (MOFs). This is partly due to the difficulties in obtaining stable secondary structures from the short α‐peptide sequences. Here we report the design, crystal conformations, coordination site dependent different silver coordinated frameworks of short α,γ‐hybrid peptide 12‐helices consisting of...

article

Artificial β‐Double Helices from Achiral γ‐Peptides

Rajkumar Misra, Sanjit Dey, Rahi M. Reja, Hosahudya N. Gopi

Angewandte Chemie International Edition > 57 > 4 > 1057 - 1061

Double helices are not common in polypeptides and proteins except in the peptide antibiotic gramicidin A and analogous l,d‐peptides. In contrast to natural polypeptides, remarkable β‐double‐helical structures from achiral γ‐peptides built from α,β‐unsaturated γ‐amino acids have been observed. The crystal structures suggest that they adopted parallel β‐double helical structures and these structures...

article

Artificial β‐Double Helices from Achiral γ‐Peptides

Rajkumar Misra, Sanjit Dey, Rahi M. Reja, Hosahudya N. Gopi

Angewandte Chemie > 130 > 4 > 1069 - 1073

Double helices are not common in polypeptides and proteins except in the peptide antibiotic gramicidin A and analogous l,d‐peptides. In contrast to natural polypeptides, remarkable β‐double‐helical structures from achiral γ‐peptides built from α,β‐unsaturated γ‐amino acids have been observed. The crystal structures suggest that they adopted parallel β‐double helical structures and these structures...

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Modulating the Structural Properties of α,γ‐Hybrid Peptides by α‐Amino Acid Residues: Uniform 12‐Helix Versus “Mixed” 12/10‐Helix

Rajkumar Misra, K. Muruga Poopathi Raja, Hans‐Jörg Hofmann, Hosahudya N. Gopi

Chemistry – A European Journal > 23 > 65 > 16644 - 16652

The most important natural α‐ and 3₁₀‐helices are stabilized by unidirectional intramolecular hydrogen bonds along the helical cylinder. In contrast, we report here on 12/10‐helical conformations with alternately changing hydrogen‐bond directionality in sequences of α,γ‐hybrid peptides P1–P5 [P1: Boc‐Ala‐Aic‐Ala‐Aic‐COOH; P2: Boc‐Leu‐Aic‐Leu‐Aic‐OEt; P3: Boc‐Leu‐Aic‐Leu‐Aic‐Leu‐Aic‐Aib‐OMe; P4: Boc‐Ala‐Aic‐Ala‐Aic‐Ala‐Aic‐Ala‐OMe;...

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Structural Dimorphism of Achiral α,γ‐Hybrid Peptide Foldamers: Coexistence of 12‐ and 15/17‐Helices

Rajkumar Misra, Abhijith Saseendran, Gijo George, Kuruva Veeresh, more

Chemistry – A European Journal > 23 > 15 > 3764 - 3772

Here, novel 12‐helices in α,γ‐hybrid peptides composed of achiral α‐aminoisobutyric acid (Aib) and 4‐aminoisocaproic acid (Aic, doubly homologated Aib) monomers in 1:1 alternation are reported. The 12‐helices were indicated by solution and crystal structural analyses of tetra‐ and heptapeptides. Surprisingly, single crystals of the longer nonapeptide displayed two different helix types: the novel...

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Non‐classical Helices with cis Carbon–Carbon Double Bonds in the Backbone: Structural Features of α,γ‐Hybrid Peptide Foldamers

Mothukuri Ganesh Kumar, Varsha J. Thombare, Mona M. Katariya, Kuruva Veeresh, more

Angewandte Chemie > 128 > 27 > 7978 - 7982

The impact of geometrically constrained cis α,β‐unsaturated γ‐amino acids on the folding of α,γ‐hybrid peptides was investigated. Structure analysis in single crystals and in solution revealed that the cis carbon–carbon double bonds can be accommodated into the 12‐helix without deviation from the overall helical conformation. The helical structures are stabilized by 4→1 hydrogen bonding in a similar...

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Non‐classical Helices with cis Carbon–Carbon Double Bonds in the Backbone: Structural Features of α,γ‐Hybrid Peptide Foldamers

Mothukuri Ganesh Kumar, Varsha J. Thombare, Mona M. Katariya, Kuruva Veeresh, more

Angewandte Chemie International Edition > 55 > 27 > 7847 - 7851

The impact of geometrically constrained cis α,β‐unsaturated γ‐amino acids on the folding of α,γ‐hybrid peptides was investigated. Structure analysis in single crystals and in solution revealed that the cis carbon–carbon double bonds can be accommodated into the 12‐helix without deviation from the overall helical conformation. The helical structures are stabilized by 4→1 hydrogen bonding in a similar...

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Synthesis of Tetrasubstituted Symmetrical Pyrazines from β‐Keto γ‐Amino Esters: A Mild Strategy for Self‐Dimerization of Peptides

Mothukuri Ganesh Kumar, Varsha J. Thombare, Rupal D. Bhaisare, Anindita Adak, more

European Journal of Organic Chemistry > 2015 > 1 > 135 - 141

A facile synthesis of highly symmetrical tetrasubstituted pyrazines through simple aerial oxidation of β‐keto γ‐amino esters is reported. The scope of the reaction was examined by use of various amino acid side‐chain functional groups and peptides. The mild and efficient transformation of β‐keto γ‐amino esters into pyrazines may serve as an attractive strategy for self‐dimerization of peptides.

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Foldamers to Nanotubes: Influence of Amino Acid Side Chains in the Hierarchical Assembly of α,γ⁴‐Hybrid Peptide Helices

Sandip V. Jadhav, Rajkumar Misra, Hosahudya N. Gopi

Chemistry – A European Journal > 20 > 50 > 16523 - 16528

Supramolecular assembly of various artificially folded 12‐helical architectures composed of γ⁴‐Val, γ⁴‐Leu and γ⁴‐Phe residues is investigated. In contrast to the 12‐helices composed of γ⁴‐Val and γ⁴‐Leu residues, the helices with γ⁴‐Phe residues displayed unique elongated nanotubular architectures. The elongated nanotube assembly was further explored as a template for biomineralization of silver...

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Efficient Access to Enantiopure γ⁴‐Amino Acids with Proteinogenic Side‐Chains and Structural Investigation of γ⁴‐Asn and γ⁴‐Ser in Hybrid Peptide Helices

Sandip V. Jadhav, Rajkumar Misra, Sumeet K. Singh, Hosahudya N. Gopi

Chemistry – A European Journal > 19 > 48 > 16256 - 16262

Hybrid peptides composed of α‐ and β‐amino acids have recently emerged as new class of peptide foldamers. Comparatively, γ‐ and hybrid γ‐peptides composed of γ⁴‐amino acids are less studied than their β‐counterparts. However, recent investigations reveal that γ⁴‐amino acids have a higher propensity to fold into ordered helical structures. As amino acid side‐chain functional groups play a crucial role...

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A Designed Three‐Stranded β‐Sheet in an α/β Hybrid Peptide

Rajesh Sonti, Hosahudya N. Gopi, Umashankara Muddegowda, Srinivasarao Ragothama, more

Chemistry – A European Journal > 19 > 19 > 5955 - 5965

The incorporation of β‐amino acid residues into the antiparallel β‐strand segments of a multi‐stranded β‐sheet peptide is demonstrated for a 19‐residue peptide, Boc‐LV^βFV^DPGL^βFVVL^DPGLVL^βFVV‐OMe (BBH19). Two centrally positioned ^DPro–Gly segments facilitate formation of a stable three‐stranded β‐sheet, in which β‐phenylalanine (^βPhe) residues occur at facing positions 3, 8 and 17. Structure determination...

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Synthesis and Structural Investigations of Functionalizable Hybrid β-Hairpin

Anupam Bandyopadhyay, Sachitanand M. Mali, Pooja Lunawat, K. Muruga Poopathi Raja, more

Organic Letters > 2011 > 13 > 17 > 4482 - 4485

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An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

Ethan A. Englund, Hosahudya N. Gopi, Daniel H. Appella

Organic Letters > 2004 > 6 > 5 > 859 - 859

article

An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

Ethan A. Englund, Hosahudya N. Gopi, Daniel H. Appella

Organic Letters > 2004 > 6 > 2 > 213 - 215

article

Stage-specific profiling of Plasmodium falciparum proteases using an internally quenched multispecificity protease substrate

Priyaranjan Pattanaik, Bimba Jain, Gudihal Ravindra, Hosahudya N. Gopi, more

Biochemical and Biophysical Research Communications > 2003 > 309 > 4 > 974-979

Novel internally quenched fluorescence peptide substrates containing sequence specific sites for cleavage by multiple proteases were designed and synthesized. The 28 and 29 residue peptides contain an N-terminal fluorescence acceptor group, 4-(4-dimethylaminophenylazo)benzoic acid (DABCYL), and a C-terminal fluorescence donor group, 5-(2-aminoethylamino)naphthalene-1-sulfonic acid (EDANS). Efficient...

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Proteolytic stability of β-peptide bonds probed using quenched fluorescent substrates incorporating a hemoglobin cleavage site

Hosahudya N. Gopi, Gudihal Ravindra, Prajna P. Pal, Priyaranjan Pattanaik, more

FEBS Letters > 2003 > 535 > 1-3 > 175-178

A set of designed internally quenched fluorescence peptide substrates has been used to probe the effects of insertion of β-peptide bonds into peptide sequences. The test sequence chosen corresponds to a proteolytically susceptible site in hemoglobin α-chain, residues 32-37. Fluorescence and mass spectral measurements demonstrate that the insertion of an β-residues at the potential cleavage sites completely...

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Search results for: Hosahudya N. Gopi

Metal‐Coordinated Supramolecular Polymers from the Minimalistic Hybrid Peptide Foldamers

Metal‐Coordinated Supramolecular Polymers from the Minimalistic Hybrid Peptide Foldamers

Structural Investigation of Hybrid Peptide Foldamers Composed of α‐Dipeptide Equivalent β‐Oxy‐δ⁵‐amino Acids

Metal‐Helix Frameworks from Short Hybrid Peptide Foldamers

Metal‐Helix Frameworks from Short Hybrid Peptide Foldamers

Artificial β‐Double Helices from Achiral γ‐Peptides

Artificial β‐Double Helices from Achiral γ‐Peptides

Modulating the Structural Properties of α,γ‐Hybrid Peptides by α‐Amino Acid Residues: Uniform 12‐Helix Versus “Mixed” 12/10‐Helix

Structural Dimorphism of Achiral α,γ‐Hybrid Peptide Foldamers: Coexistence of 12‐ and 15/17‐Helices

Non‐classical Helices with cis Carbon–Carbon Double Bonds in the Backbone: Structural Features of α,γ‐Hybrid Peptide Foldamers

Non‐classical Helices with cis Carbon–Carbon Double Bonds in the Backbone: Structural Features of α,γ‐Hybrid Peptide Foldamers

Synthesis of Tetrasubstituted Symmetrical Pyrazines from β‐Keto γ‐Amino Esters: A Mild Strategy for Self‐Dimerization of Peptides

Foldamers to Nanotubes: Influence of Amino Acid Side Chains in the Hierarchical Assembly of α,γ⁴‐Hybrid Peptide Helices

Efficient Access to Enantiopure γ⁴‐Amino Acids with Proteinogenic Side‐Chains and Structural Investigation of γ⁴‐Asn and γ⁴‐Ser in Hybrid Peptide Helices

A Designed Three‐Stranded β‐Sheet in an α/β Hybrid Peptide

Synthesis and Structural Investigations of Functionalizable Hybrid β-Hairpin

An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

Stage-specific profiling of Plasmodium falciparum proteases using an internally quenched multispecificity protease substrate

Proteolytic stability of β-peptide bonds probed using quenched fluorescent substrates incorporating a hemoglobin cleavage site

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