60
2 Synthesis of In-Tether Chiral Center Peptides …
References
1. Yin H, Hamilton AD (2005) Strategies for targeting protein-protein interactions with synthetic
agents. Angew Chem Int Ed 44:4130–4163
2. Azzarito V, Long K, Murphy NS, Wilson AJ (2013) Inhibition of [alpha]-helix-mediated
protein-protein interactions using designed molecules. Nat Chem 5:161–173
3. Milroy L-G, Grossmann TN, Hennig S, Brunsveld L, Ottmann C (2014) Modulators of proteinprotein interactions. Chem Rev 114:4695–4748
4. Osapay G, Taylor JW (1990) Multicyclic polypeptide model compounds: 1. Synthesis of
a tricyclic amphiphilic.alpha.-helical peptide using an oxime resin, segment-condensation
approach. J Am Chem Soc 112:6046–6051
5. Phelan JC, Skelton NJ, Braisted AC, McDowell RS (1997) A general method for constraining
short peptides to an α-helical conformation. J Am Chem Soc 119:455–460
6. Pease JHB, Storrs RW, Wemmer DE (1990) Folding and activity of hybrid sequence, disulfidestabilized peptides. Proc Natl Acad Sci U S A 87:5643–5647
7. Jackson DY, King DS, Chmielewski J, Singh S, Schultz PG (1991) General approach to the
synthesis of short.alpha.-helical peptides. J Am Chem Soc 113:9391–9392
8. Cabezas E, Satterthwait AC (1999) The hydrogen bond mimic approach: solid-phase synthesis
of a peptide stabilized as an α-helix with a hydrazone link. J Am Chem Soc 121:3862–3875
9. Kumita JR, Smart OS, Woolley GA (2000) Photo-control of helix content in a short peptide.
Proc Natl Acad Sci U S A 97:3803–3808
10. Schafmeister CE, Po J, Verdine GL (2000) An all-hydrocarbon cross-linking system for
enhancing the helicity and metabolic stability of peptides. J Am Chem Soc 122:5891–5892
11. Leduc AM, Trent JO, Wittliff JL, Bramlett KS, Briggs SL, Chirgadze NY, Wang Y, Burris TP,
Spatola AF (2003) Helix-stabilized cyclic peptides as selective inhibitors of steroid receptorcoactivator interactions. Proc Natl Acad Sci U S A 100:11273–11278
12. Galande AK, Bramlett KS, Burris TP, Wittliff JL, Spatola AF (2004) Thioether side
chain cyclization for helical peptide formation: inhibitors of estrogen receptor–coactivator
interactions. J Pept Res 63:297–302
13. Shepherd NE, Hoang HN, Abbenante G, Fairlie DP (2005) Single turn peptide alpha helices
with exceptional stability in water. J Am Chem Soc 127:2974–2983
14. Cantel S, Le Chevalier Isaad A, Scrima M, Levy JJ, DiMarchi RD, Rovero P, Halperin JA,
D’Ursi AM, Papini AM, Chorev M (2008) Synthesis and conformational analysis of a cyclic
peptide obtained via i to i + 4 intramolecular side-chain to side-chain azide − alkyne 1,
3-Dipolar cycloaddition. J Org Chem 73:5663–5674
15. Muppidi A, Wang Z, Li X, Chen J, Lin Q (2011) Achieving cell penetration with distancematching cysteine cross-linkers: a facile route to cell-permeable peptide dual inhibitors of
Mdm2/Mdmx. Chem Commun 47:9396–9398
16. Lau YH, de Andrade P, Quah ST, Rossmann M, Laraia L, Skold N, Sum TJ, Rowling PJE, Joseph
TL, Verma C, Hyvonen M, Itzhaki LS, Venkitaraman AR, Brown CJ, Lane DP, Spring DR
(2014) Functionalised staple linkages for modulating the cellular activity of stapled peptides.
Chem Sci 5:1804–1809
17. Haney CM, Horne WS (2014) Dynamic covalent side-chain cross-links via intermolecular
oxime or hydrazone formation from bifunctional peptides and simple organic linkers. J Pept
Sci 20:108–114
18. Zou Y, Spokoyny AM, Zhang C, Simon MD, Yu H, Lin Y-S, Pentelute BL (2014) Convergent
diversity-oriented side-chain macrocyclization scan for unprotected polypeptides. Org Biomol
Chem 12:566–573
19. Hilinski GJ, Kim Y-W, Hong J, Kutchukian PS, Crenshaw CM, Berkovitch SS, Chang A, Ham
S, Verdine GL (2014) Stitched α-helical peptides via bis ring-closing metathesis. J Am Chem
Soc 136:12314–12322
20. Mazzier D, Peggion C, Toniolo C, Moretto A (2014) Enhancement of the helical content
and stability induced in a linear oligopeptide by an i, i + 4 intramolecularly double stapled,
overlapping, bicyclic 31,22,5—(E)ene Motif. Biopolymers 102:115–123
2 Synthesis of In-Tether Chiral Center Peptides …
References
1. Yin H, Hamilton AD (2005) Strategies for targeting protein-protein interactions with synthetic
agents. Angew Chem Int Ed 44:4130–4163
2. Azzarito V, Long K, Murphy NS, Wilson AJ (2013) Inhibition of [alpha]-helix-mediated
protein-protein interactions using designed molecules. Nat Chem 5:161–173
3. Milroy L-G, Grossmann TN, Hennig S, Brunsveld L, Ottmann C (2014) Modulators of proteinprotein interactions. Chem Rev 114:4695–4748
4. Osapay G, Taylor JW (1990) Multicyclic polypeptide model compounds: 1. Synthesis of
a tricyclic amphiphilic.alpha.-helical peptide using an oxime resin, segment-condensation
approach. J Am Chem Soc 112:6046–6051
5. Phelan JC, Skelton NJ, Braisted AC, McDowell RS (1997) A general method for constraining
short peptides to an α-helical conformation. J Am Chem Soc 119:455–460
6. Pease JHB, Storrs RW, Wemmer DE (1990) Folding and activity of hybrid sequence, disulfidestabilized peptides. Proc Natl Acad Sci U S A 87:5643–5647
7. Jackson DY, King DS, Chmielewski J, Singh S, Schultz PG (1991) General approach to the
synthesis of short.alpha.-helical peptides. J Am Chem Soc 113:9391–9392
8. Cabezas E, Satterthwait AC (1999) The hydrogen bond mimic approach: solid-phase synthesis
of a peptide stabilized as an α-helix with a hydrazone link. J Am Chem Soc 121:3862–3875
9. Kumita JR, Smart OS, Woolley GA (2000) Photo-control of helix content in a short peptide.
Proc Natl Acad Sci U S A 97:3803–3808
10. Schafmeister CE, Po J, Verdine GL (2000) An all-hydrocarbon cross-linking system for
enhancing the helicity and metabolic stability of peptides. J Am Chem Soc 122:5891–5892
11. Leduc AM, Trent JO, Wittliff JL, Bramlett KS, Briggs SL, Chirgadze NY, Wang Y, Burris TP,
Spatola AF (2003) Helix-stabilized cyclic peptides as selective inhibitors of steroid receptorcoactivator interactions. Proc Natl Acad Sci U S A 100:11273–11278
12. Galande AK, Bramlett KS, Burris TP, Wittliff JL, Spatola AF (2004) Thioether side
chain cyclization for helical peptide formation: inhibitors of estrogen receptor–coactivator
interactions. J Pept Res 63:297–302
13. Shepherd NE, Hoang HN, Abbenante G, Fairlie DP (2005) Single turn peptide alpha helices
with exceptional stability in water. J Am Chem Soc 127:2974–2983
14. Cantel S, Le Chevalier Isaad A, Scrima M, Levy JJ, DiMarchi RD, Rovero P, Halperin JA,
D’Ursi AM, Papini AM, Chorev M (2008) Synthesis and conformational analysis of a cyclic
peptide obtained via i to i + 4 intramolecular side-chain to side-chain azide − alkyne 1,
3-Dipolar cycloaddition. J Org Chem 73:5663–5674
15. Muppidi A, Wang Z, Li X, Chen J, Lin Q (2011) Achieving cell penetration with distancematching cysteine cross-linkers: a facile route to cell-permeable peptide dual inhibitors of
Mdm2/Mdmx. Chem Commun 47:9396–9398
16. Lau YH, de Andrade P, Quah ST, Rossmann M, Laraia L, Skold N, Sum TJ, Rowling PJE, Joseph
TL, Verma C, Hyvonen M, Itzhaki LS, Venkitaraman AR, Brown CJ, Lane DP, Spring DR
(2014) Functionalised staple linkages for modulating the cellular activity of stapled peptides.
Chem Sci 5:1804–1809
17. Haney CM, Horne WS (2014) Dynamic covalent side-chain cross-links via intermolecular
oxime or hydrazone formation from bifunctional peptides and simple organic linkers. J Pept
Sci 20:108–114
18. Zou Y, Spokoyny AM, Zhang C, Simon MD, Yu H, Lin Y-S, Pentelute BL (2014) Convergent
diversity-oriented side-chain macrocyclization scan for unprotected polypeptides. Org Biomol
Chem 12:566–573
19. Hilinski GJ, Kim Y-W, Hong J, Kutchukian PS, Crenshaw CM, Berkovitch SS, Chang A, Ham
S, Verdine GL (2014) Stitched α-helical peptides via bis ring-closing metathesis. J Am Chem
Soc 136:12314–12322
20. Mazzier D, Peggion C, Toniolo C, Moretto A (2014) Enhancement of the helical content
and stability induced in a linear oligopeptide by an i, i + 4 intramolecularly double stapled,
overlapping, bicyclic 31,22,5—(E)ene Motif. Biopolymers 102:115–123