title: Rational construction of triazole/urea based peptidomimetic macrocycles as pseudocyclo-β-peptides and studies on their chirality controlled self-assembly.
abstract: A tandem macro-dimerization reaction via a Cu(I) catalyzed azide/alkyne cycloaddition reaction has been employed to construct triazole/urea based peptidomimetic macrocycles considered as pseudocyclo-β-peptides. Introduction of one particular chirality in the peptide backbone can alter the conformation as well as nature of self-assembly from cyclic D-,L-,α-peptide to cyclo-β-peptide. One of them (16a) forms antiparallel dimers while the other (16b) undergoes higher order aggregation to form a nanorod structure.
authors.affiliation: Chemistry Division, CSIR-Indian Institute of Chemical Biology , Kolkata, 700032, India.
authors.forename: Abhijit
authors.initials: A
authors.lastname: Ghorai
authors.forename: Samanth
authors.initials: S
authors.lastname: Reddy K
authors.forename: Basudeb
authors.initials: B
authors.lastname: Achari
authors.forename: Partha
authors.initials: P
authors.lastname: Chattopadhyay
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D019281:Dimerization; D007454:Iodides / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D043942:Nanotubes / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D057786:Peptidomimetics; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*; D014508:Urea / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D007454:Iodides; D010456:Peptides, Cyclic; D057786:Peptidomimetics; D014230:Triazoles; D003300:Copper; C073870:cuprous iodide; D014508:Urea