Glycylglycine Rotaxanes—The Hydrogen Bond Directed Assembly of Synthetic Peptide Rotaxanes
Corresponding Author
Dr. David A. Leigh
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]Search for more papers by this authorAden Murphy
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]
Search for more papers by this authorDr. John P. Smart
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]
Search for more papers by this authorAlexandra M. Z. Slawin
Molecular Structure Laboratory, Department of Chemistry, University of Loughborough (UK)
Search for more papers by this authorCorresponding Author
Dr. David A. Leigh
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]Search for more papers by this authorAden Murphy
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]
Search for more papers by this authorDr. John P. Smart
Department of Chemistry, University of Manchester Institute of Science and Technology, Sackville Street, Manchester M601QD (UK), Fax: Int. code +(161) 200-4539, e-mail: [email protected]
Search for more papers by this authorAlexandra M. Z. Slawin
Molecular Structure Laboratory, Department of Chemistry, University of Loughborough (UK)
Search for more papers by this authorGraphical Abstract
Ringing a peptide (not-so-dumb)bell: the amide groups in the glycylglycine derivative shown below provide the information required to template the formation of benzylic amide macrocycles to yield peptide [2]rotaxanes. The four key hydrogen bonds responsible for cyclization remain intact in the rotaxane in nonpolar solvents, in the solid state, and (when X = N) even in polar solvents such as [D6]DMSO and [D6]DMSO/D2O mixtures. X = CH, N; shaded sphere = Ph2CH, black sphere = Ph2CHCH2.
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- 37 Crystal data for 9: C62H57O8.50N8, Mr = 1050.18, clear cyrstal of dimensions 0.15 × 0.2 × 0.66 mm, monoclinic, space group P21/n (no. 14); a = 18.172(2), b = 16.874(4), c = 18.259(38) Å, β = 92.34(1)°, V = 5594(1) Å3, ρcalcd = 1.247 gcm−3, Z = 4; 8950 reflections measured, 8645 unique. Diffractometer Rigaku AFC7S, 2θmax = 120.1°, CuKα radiation, λ = 1.54178 Å, T = 296 K. The structure was solved by direct methods (SIR92) [33] and subjected to least-squares refinement (TEXSAN [34]) to yield final residuals of R = 0.061 and Rw = 0.045 for 713 parameters. All hydrogen atoms were placed in chemically reasonable positions. Crystallograhic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as Supplementary publication no. CCDC-179-100060. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: Int. code +(1223) 336-033; e-mail: [email protected])
