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21. Andrews MJI, Tabor AB (1999) Forming stable helical peptides using natural and artificial
amino acids. Tetrahedron 55:11711–11743
22. Henchey LK, Jochim AL, Arora PS (2008) Contemporary strategies for the stabilization of
peptides in the alpha-helical conformation. Curr Opin Chem Biol 12:692–697
23. Hill TA, Shepherd NE, Diness F, Fairlie DP (2014) Constraining cyclic peptides to mimic
protein structure motifs. Angew Chem Int Ed Engl 53:13020–13041
24. Walensky LD, Bird GH (2014) Hydrocarbon-stapled peptides: principles, practice, and
progress. J Med Chem 57:6275–6288
25. Lau YH, de Andrade P, Wu Y, Spring DR (2015) Peptide stapling techniques based on different
macrocyclisation chemistries. Chem Soc Rev 44:91–102
26. Bracken C, Gulyas J, Taylor JW, Baum J (1994) Synthesis and nuclear-magnetic-resonance
structure determination of an alpha-helical, bicyclic, lactam-bridged hexapeptide. J Am Chem
Soc 116:6431–6432
27. Blackwell HE, Grubbs RH (1998) Highly efficient synthesis of covalently cross-linked peptide
helices by ring-closing metathesis. Angew Chem Int Ed 37:3281–3284
28. Walensky LD, Kung AL, Escher I, Malia TJ, Barbuto S, Wright RD, Wagner G, Verdine GL,
Korsmeyer SJ (2004) Activation of apoptosis in vivo by a hydrocarbon-stapled bh3 helix.
Science 305:1466–1470
29. Moellering RE, Cornejo M, Davis TN, Bianco CD, Aster JC, Blacklow SC, Kung AL, Gilliland
DG, Verdine GL, Bradner JE (2009) Direct inhibition of the NOTCH transcription factor
complex. Nature 462:182–188
30. Stewart ML, Fire E, Keating AE, Walensky LD (2010) The MCL-1 BH3 helix is an exclusive
MCL-1 inhibitor and apoptosis sensitizer. Nat Chem Biol 6:595–601
31. Baek S, Kutchukian PS, Verdine GL, Huber R, Holak TA, Lee KW, Popowicz GM (2012)
Structure of the stapled p53 peptide bound to Mdm2. J Am Chem Soc 134:103–106
32. Chang YS, Graves B, Guerlavais V, Tovar C, Packman K, To K-H, Olson KA, Kesavan K,
Gangurde P, Mukherjee A, Baker T, Darlak K, Elkin C, Filipovic Z, Qureshi FZ, Cai H, Berry
P, Feyfant E, Shi XE, Horstick J, Annis DA, Manning AM, Fotouhi N, Nash H, Vassilev LT,
Sawyer TK (2013) Stapled alpha-helical peptide drug development: a potent dual inhibitor of
MDM2 and MDMX for p53-dependent cancer therapy. Proc Natl Acad Sci U S A 110:E3445–
E3454
33. Sinclair JKL, Denton EV, Schepartz A (2014) Inhibiting epidermal growth factor receptor at a
distance. J Am Chem Soc 136:11232–11235
34. Chapman RN, Dimartino G, Arora PS (2004) A highly stable short α-helix constrained by a
main-chain hydrogen-bond surrogate. J Am Chem Soc 126:12252–12253
35. Wang D, Liao W, Arora PS (2005) Enhanced metabolic stability and protein-binding properties
of artificial alpha helices derived from a hydrogen-bond surrogate: application to Bcl-xL.
Angew Chem Int Edit 44:6525–6529
36. Liu J, Wang D, Zheng Q, Lu M, Arora PS (2008) Atomic structure of a short α-helix stabilized
by a main chain hydrogen-bond surrogate. J Am Chem Soc 130:4334–4337
37. Henchey LK, Kushal S, Dubey R, Chapman RN, Olenyuk BZ, Arora PS (2010) Inhibition of
hypoxia inducible factor 1—transcription coactivator interaction by a hydrogen bond surrogate
α-helix. J Am Chem Soc 132:941–943
38. Frost JR, Vitali F, Jacob NT, Brown MD, Fasan R (2013) Macrocyclization of organo-peptide
hybrids through a dual bio-orthogonal ligation: insights from structure-reactivity studies. Chem
Bio Chem 14:147–160
39. Jo H, Meinhardt N, Wu Y, Kulkarni S, Hu X, Low KE, Davies PL, DeGrado WF, Greenbaum
DC (2012) Development of α-helical calpain probes by mimicking a natural protein-protein
interaction. J Am Chem Soc 134:17704–17713
40. Muppidi A, Li XL, Chen JD, Lin Q (2011) Conjugation of spermine enhances cellular uptake of
the stapled peptide-based inhibitors of p53-Mdm2 interaction. Bioorg Med Chem Lett 21:7412–
7415
41. Phillips C, Roberts LR, Schade M, Bazin R, Bent A, Davies NL, Moore R, Pannifer AD,
Pickford AR, Prior SH, Read CM, Scott A, Brown DG, Xu B, Irving SL (2011) Design and
structure of stapled peptides binding to estrogen receptors. J Am Chem Soc 133:9696–9699
61
21. Andrews MJI, Tabor AB (1999) Forming stable helical peptides using natural and artificial
amino acids. Tetrahedron 55:11711–11743
22. Henchey LK, Jochim AL, Arora PS (2008) Contemporary strategies for the stabilization of
peptides in the alpha-helical conformation. Curr Opin Chem Biol 12:692–697
23. Hill TA, Shepherd NE, Diness F, Fairlie DP (2014) Constraining cyclic peptides to mimic
protein structure motifs. Angew Chem Int Ed Engl 53:13020–13041
24. Walensky LD, Bird GH (2014) Hydrocarbon-stapled peptides: principles, practice, and
progress. J Med Chem 57:6275–6288
25. Lau YH, de Andrade P, Wu Y, Spring DR (2015) Peptide stapling techniques based on different
macrocyclisation chemistries. Chem Soc Rev 44:91–102
26. Bracken C, Gulyas J, Taylor JW, Baum J (1994) Synthesis and nuclear-magnetic-resonance
structure determination of an alpha-helical, bicyclic, lactam-bridged hexapeptide. J Am Chem
Soc 116:6431–6432
27. Blackwell HE, Grubbs RH (1998) Highly efficient synthesis of covalently cross-linked peptide
helices by ring-closing metathesis. Angew Chem Int Ed 37:3281–3284
28. Walensky LD, Kung AL, Escher I, Malia TJ, Barbuto S, Wright RD, Wagner G, Verdine GL,
Korsmeyer SJ (2004) Activation of apoptosis in vivo by a hydrocarbon-stapled bh3 helix.
Science 305:1466–1470
29. Moellering RE, Cornejo M, Davis TN, Bianco CD, Aster JC, Blacklow SC, Kung AL, Gilliland
DG, Verdine GL, Bradner JE (2009) Direct inhibition of the NOTCH transcription factor
complex. Nature 462:182–188
30. Stewart ML, Fire E, Keating AE, Walensky LD (2010) The MCL-1 BH3 helix is an exclusive
MCL-1 inhibitor and apoptosis sensitizer. Nat Chem Biol 6:595–601
31. Baek S, Kutchukian PS, Verdine GL, Huber R, Holak TA, Lee KW, Popowicz GM (2012)
Structure of the stapled p53 peptide bound to Mdm2. J Am Chem Soc 134:103–106
32. Chang YS, Graves B, Guerlavais V, Tovar C, Packman K, To K-H, Olson KA, Kesavan K,
Gangurde P, Mukherjee A, Baker T, Darlak K, Elkin C, Filipovic Z, Qureshi FZ, Cai H, Berry
P, Feyfant E, Shi XE, Horstick J, Annis DA, Manning AM, Fotouhi N, Nash H, Vassilev LT,
Sawyer TK (2013) Stapled alpha-helical peptide drug development: a potent dual inhibitor of
MDM2 and MDMX for p53-dependent cancer therapy. Proc Natl Acad Sci U S A 110:E3445–
E3454
33. Sinclair JKL, Denton EV, Schepartz A (2014) Inhibiting epidermal growth factor receptor at a
distance. J Am Chem Soc 136:11232–11235
34. Chapman RN, Dimartino G, Arora PS (2004) A highly stable short α-helix constrained by a
main-chain hydrogen-bond surrogate. J Am Chem Soc 126:12252–12253
35. Wang D, Liao W, Arora PS (2005) Enhanced metabolic stability and protein-binding properties
of artificial alpha helices derived from a hydrogen-bond surrogate: application to Bcl-xL.
Angew Chem Int Edit 44:6525–6529
36. Liu J, Wang D, Zheng Q, Lu M, Arora PS (2008) Atomic structure of a short α-helix stabilized
by a main chain hydrogen-bond surrogate. J Am Chem Soc 130:4334–4337
37. Henchey LK, Kushal S, Dubey R, Chapman RN, Olenyuk BZ, Arora PS (2010) Inhibition of
hypoxia inducible factor 1—transcription coactivator interaction by a hydrogen bond surrogate
α-helix. J Am Chem Soc 132:941–943
38. Frost JR, Vitali F, Jacob NT, Brown MD, Fasan R (2013) Macrocyclization of organo-peptide
hybrids through a dual bio-orthogonal ligation: insights from structure-reactivity studies. Chem
Bio Chem 14:147–160
39. Jo H, Meinhardt N, Wu Y, Kulkarni S, Hu X, Low KE, Davies PL, DeGrado WF, Greenbaum
DC (2012) Development of α-helical calpain probes by mimicking a natural protein-protein
interaction. J Am Chem Soc 134:17704–17713
40. Muppidi A, Li XL, Chen JD, Lin Q (2011) Conjugation of spermine enhances cellular uptake of
the stapled peptide-based inhibitors of p53-Mdm2 interaction. Bioorg Med Chem Lett 21:7412–
7415
41. Phillips C, Roberts LR, Schade M, Bazin R, Bent A, Davies NL, Moore R, Pannifer AD,
Pickford AR, Prior SH, Read CM, Scott A, Brown DG, Xu B, Irving SL (2011) Design and
structure of stapled peptides binding to estrogen receptors. J Am Chem Soc 133:9696–9699