62
2 Synthesis of In-Tether Chiral Center Peptides …
42. Assem N, Ferreira DJ, Wolan DW, Dawson PE (2015) Acetone-linked peptides: a convergent
approach for peptide macrocyclization and labeling. Angew Chem Int Edit 54:8665–8668
43. Brown SP, Smith AB (2015) Peptide/protein stapling and unstapling: introduction of s-tetrazine,
photochemical release, and regeneration of the peptide/protein. J Am Chem Soc 137:4034–4037
44. Boguslavsky V, Hruby VJ, O’Brien DF, Misicka A, Lipkowski AW (2003) Effect of peptide
conformation on membrane permeability. J Pept Res 61:287–297
45. Rezai T, Yu B, Millhauser GL, Jacobson MP, Lokey RS (2006) Testing the conformational
hypothesis of passive membrane permeability using synthetic cyclic peptide diastereomers. J
Am Chem Soc 128:2510–2511
46. Rezai T, Bock JE, Zhou MV, Kalyanaraman C, Lokey RS, Jacobson MP (2006) Conformational
flexibility, internal hydrogen bonding, and passive membrane permeability: successful in Silico
prediction of the relative permeabilities of cyclic peptides. J Am Chem Soc 128:14073–14080
47. Chu Q, Moellering RE, Hilinski GJ, Kim YW, Grossmann TN, Yeh JTH, Verdine GL (2015)
Towards understanding cell penetration by stapled peptides. Med chem comm 6:111–119
48. Belokon YN, Tararov VI, Maleev VI, Savel’eva TF, Ryzhov MG (1998) Improved procedures for the synthesis of (S)-2-[N-(N -benzylprolyl)amino] benzophenone (BPB) and Ni(II)
complexes of Schiff’s bases derived from BPB and amino acids. Tetrahedron Asymmetry
9:4249–4252
49. Tang X, Soloshonok VA, Hruby VJ (2000) Convenient, asymmetric synthesis of enantiomerically pure 2 ,6 -dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic
glycine. Tetrahedron Asymmetry 11:2917–2925
50. Qiu W, Soloshonok VA, Cai C, Tang X, Hruby VJ (2000) Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine. Tetrahedron
56:2577–2582
51. Soloshonok VA, Tang X, Hruby VJ (2001) Large-scale asymmetric synthesis of novel sterically
constrained 2 ,6 -dimethyl- and α,2 ,6 -trimethyltyrosine and -phenylalanine derivatives via
alkylation of chiral equivalents of nucleophilic glycine and alanine. Tetrahedron 57:6375–6382
52. Aillard B, Robertson NS, Baldwin AR, Robins S, Jamieson AG (2014) Robust asymmetric
synthesis of unnatural alkenyl amino acids for conformationally constrained [small alpha]-helix
peptides. Org Biomol Chem 12:8775–8782
53. Wüthrich K, Billeter M, Braun W (1984) Polypeptide secondary structure determination by
nuclear magnetic resonance observation of short proton-proton distances. J Mol Biol 180:715–
740
54. Hu B, Gilkes DM, Chen J (2007) Efficient p53 activation and apoptosis by simultaneous
disruption of binding to MDM2 and MDMX. Cancer Res 67:8810–8817
55. Pflugrath J (1999) The finer things in X-ray diffraction data collection. Acta Crystallogr Sect
D 55:1718–1725
56. Sheldrick GM (2010) Experimental phasing with SHELXC/D/E: combining chain tracing with
density modification. Acta Crystallogr Sect D-Biol Crystallogr 66:479–485
57. Pronk S, Páll S, Schulz R, Larsson P, Bjelkmar P, Apostolov R, Shirts MR, Smith JC, Kasson
PM, van der Spoel D, Hess B, Lindahl E (2013) GROMACS 4.5: A high-throughput and highly
parallel open source molecular simulation toolkit. Bioinformatics 29:845–854
58. Jiang F, Wu Y-D (2014) Folding of fourteen small proteins with a residue-specific force field
and replica-exchange molecular dynamics. J Am Chem Soc 136:9536–9539
59. Jiang F, Zhou C-Y, Wu Y-D (2014) Residue-specific force field based on the protein coil
library—RSFF1: modification of OPLS-AA/L. J Phys Chem B 118:6983–6998
60. Zhou C-Y, Jiang F, Wu Y-D (2015) Residue-specific force field based on protein coil library—
RSFF2: modification of AMBER ff99SB. J Phys Chem B 119:1035–1047
61. Wang J, Wolf RM, Caldwell JW, Kollman PA, Case DA (2004) Development and testing of a
general amber force field. J Comput Chem 25:1157–1174
62. Bayly C, Cieplak P, Cornell W, Kollman P (1993) A well-behaved electrostatic potential based
method using charge restraints for deriving atomic charges: the RESP model. J Phys Chem
97:10269–10280
2 Synthesis of In-Tether Chiral Center Peptides …
42. Assem N, Ferreira DJ, Wolan DW, Dawson PE (2015) Acetone-linked peptides: a convergent
approach for peptide macrocyclization and labeling. Angew Chem Int Edit 54:8665–8668
43. Brown SP, Smith AB (2015) Peptide/protein stapling and unstapling: introduction of s-tetrazine,
photochemical release, and regeneration of the peptide/protein. J Am Chem Soc 137:4034–4037
44. Boguslavsky V, Hruby VJ, O’Brien DF, Misicka A, Lipkowski AW (2003) Effect of peptide
conformation on membrane permeability. J Pept Res 61:287–297
45. Rezai T, Yu B, Millhauser GL, Jacobson MP, Lokey RS (2006) Testing the conformational
hypothesis of passive membrane permeability using synthetic cyclic peptide diastereomers. J
Am Chem Soc 128:2510–2511
46. Rezai T, Bock JE, Zhou MV, Kalyanaraman C, Lokey RS, Jacobson MP (2006) Conformational
flexibility, internal hydrogen bonding, and passive membrane permeability: successful in Silico
prediction of the relative permeabilities of cyclic peptides. J Am Chem Soc 128:14073–14080
47. Chu Q, Moellering RE, Hilinski GJ, Kim YW, Grossmann TN, Yeh JTH, Verdine GL (2015)
Towards understanding cell penetration by stapled peptides. Med chem comm 6:111–119
48. Belokon YN, Tararov VI, Maleev VI, Savel’eva TF, Ryzhov MG (1998) Improved procedures for the synthesis of (S)-2-[N-(N -benzylprolyl)amino] benzophenone (BPB) and Ni(II)
complexes of Schiff’s bases derived from BPB and amino acids. Tetrahedron Asymmetry
9:4249–4252
49. Tang X, Soloshonok VA, Hruby VJ (2000) Convenient, asymmetric synthesis of enantiomerically pure 2 ,6 -dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic
glycine. Tetrahedron Asymmetry 11:2917–2925
50. Qiu W, Soloshonok VA, Cai C, Tang X, Hruby VJ (2000) Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine. Tetrahedron
56:2577–2582
51. Soloshonok VA, Tang X, Hruby VJ (2001) Large-scale asymmetric synthesis of novel sterically
constrained 2 ,6 -dimethyl- and α,2 ,6 -trimethyltyrosine and -phenylalanine derivatives via
alkylation of chiral equivalents of nucleophilic glycine and alanine. Tetrahedron 57:6375–6382
52. Aillard B, Robertson NS, Baldwin AR, Robins S, Jamieson AG (2014) Robust asymmetric
synthesis of unnatural alkenyl amino acids for conformationally constrained [small alpha]-helix
peptides. Org Biomol Chem 12:8775–8782
53. Wüthrich K, Billeter M, Braun W (1984) Polypeptide secondary structure determination by
nuclear magnetic resonance observation of short proton-proton distances. J Mol Biol 180:715–
740
54. Hu B, Gilkes DM, Chen J (2007) Efficient p53 activation and apoptosis by simultaneous
disruption of binding to MDM2 and MDMX. Cancer Res 67:8810–8817
55. Pflugrath J (1999) The finer things in X-ray diffraction data collection. Acta Crystallogr Sect
D 55:1718–1725
56. Sheldrick GM (2010) Experimental phasing with SHELXC/D/E: combining chain tracing with
density modification. Acta Crystallogr Sect D-Biol Crystallogr 66:479–485
57. Pronk S, Páll S, Schulz R, Larsson P, Bjelkmar P, Apostolov R, Shirts MR, Smith JC, Kasson
PM, van der Spoel D, Hess B, Lindahl E (2013) GROMACS 4.5: A high-throughput and highly
parallel open source molecular simulation toolkit. Bioinformatics 29:845–854
58. Jiang F, Wu Y-D (2014) Folding of fourteen small proteins with a residue-specific force field
and replica-exchange molecular dynamics. J Am Chem Soc 136:9536–9539
59. Jiang F, Zhou C-Y, Wu Y-D (2014) Residue-specific force field based on the protein coil
library—RSFF1: modification of OPLS-AA/L. J Phys Chem B 118:6983–6998
60. Zhou C-Y, Jiang F, Wu Y-D (2015) Residue-specific force field based on protein coil library—
RSFF2: modification of AMBER ff99SB. J Phys Chem B 119:1035–1047
61. Wang J, Wolf RM, Caldwell JW, Kollman PA, Case DA (2004) Development and testing of a
general amber force field. J Comput Chem 25:1157–1174
62. Bayly C, Cieplak P, Cornell W, Kollman P (1993) A well-behaved electrostatic potential based
method using charge restraints for deriving atomic charges: the RESP model. J Phys Chem
97:10269–10280