Capping β-hairpin with N-terminal d-amino acid stabilizes peptide scaffold

Biopolymers

Volumn , Issue , 2016, Pages 260-266

  Makwana, Kamlesh M ^a   Mahalakshmi, Radhakrishnan ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL   (India)

Author keywords

aliphatic aromatic cluster; d amino acid; NMR spectroscopy; peptide design; peptide hairpin

Indexed keywords

AMINO ACIDS; AROMATIC COMPOUNDS; BIOPOLYMERS; HYDROGEN BONDS; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SCAFFOLDS;

ALIPHATIC AMINO ACIDS; AROMATIC CLUSTERS; D-AMINO ACID; MIRROR IMAGES; PEPTIDE DESIGN; PEPTIDE SCAFFOLDS; SOLUTION NMR; SYNTHETIC PEPTIDE;

PEPTIDES;

ALIPHATIC COMPOUND; DEXTRO AMINO ACID; LEUCINE; MOLECULAR SCAFFOLD; PROTON; SYNTHETIC PEPTIDE;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; BETA HAIRPIN; CAPPING PHENOMENON; CHEMICAL INTERACTION; CONFORMATION; HYDROGEN BOND; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE ANALYSIS; PROTEIN FOLDING; PROTEIN STABILITY; PROTEIN STRUCTURE; TEMPERATURE;

EID: 84978166179     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.22837     Document Type: Article

References (38)

1. Smith, C. K.; Regan, L. Acc Chem Res 1997, 30, 153–161.
2. Cochran, A. G.; Skelton, N. J.; Starovasnik, M. A. Proc Natl Acad Sci USA 2001, 98, 5578–5583.
3. Venkatraman, J.; Shankaramma, S. C.; Balaram, P. Chem Rev 2001, 101, 3131–3152.
4. Chiti, F.; Dobson, C. M. Annu Rev Biochem 2006, 75, 333–366.
5. Makwana, K. M.; Mahalakshmi, R. Protein Sci 2015, 24, 1920–1933.
6. Venkatraman, J.; Naganagowda, G. A.; Sudha, R.; Balaram, P. Chem Commun 2001, 2660–2661.
7. Robinson, J. A. Acc Chem Res 2008, 41, 1278–1288.
8. Mahajan, M.; Bhattacharjya, S. Angew Chem Int Ed 2013, 52, 6430–6434.
9. Fischer, S.; Geyer, A. Angew Chem Int Ed 2014, 53, 3849–3853.
10. Xu, L.; Chou, S.; Wang, J.; Shao, C.; Li, W.; Zhu, X.; Shan, A. Amino Acids 2015, 47, 2385–2397.
11. Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem Rev 2001, 101, 3219–3232.
12. Nowick, J. S. Acc Chem Res 2008, 41, 1319–1330.
13. Vasudev, P. G.; Chatterjee, S.; Shamala, N.; Balaram, P. Acc Chem Res 2009, 42, 1628–1639.
14. Vasudev, P. G.; Chatterjee, S.; Shamala, N.; Balaram, P. Chem Rev 2011, 111, 657–687.
15. Toniolo, C.; Crisma, M.; Moretto, A.; Peggion, C.; Formaggio, F.; Aleman, C.; Cativiela, C.; Ramakrishnan, C.; Balaram, P. Chem Eur J 2015, 21, 13866–13877.
16. Santiveri, C. M.; Leon, E.; Rico, M.; Jimenez, M. A. Chem Eur J 2008, 14, 488–499.
17. Mirassou, Y.; Santiveri, C. M.; Perez de Vega, M. J.; Gonzalez-Muniz, R.; Jimenez, M. A. ChemBioChem 2009, 10, 902–910.
18. Makwana, K. M.; Mahalakshmi, R. J Phys Chem B 2015, 119, 5376–5385.
19. Samanta, U.; Pal, D.; Chakrabarti, P. Acta Crystallogr D Biol Crystallogr 1999, 55, 1421–1427.
20. Bhattacharyya, R.; Samanta, U.; Chakrabarti, P. Protein Eng 2002, 15, 91–100.
21. Mahalakshmi, R.; Sengupta, A.; Raghothama, S.; Shamala, N.; Balaram, P. J Pept Res 2005, 66, 277–296.
22. Sengupta, A.; Mahalakshmi, R.; Shamala, N.; Balaram, P. J Pept Res 2005, 65, 113–129.
23. Mahalakshmi, R.; Sengupta, A.; Raghothama, S.; Shamala, N.; Balaram, P. Biopolymers 2007, 88, 36–54.
24. Santiveri, C. M.; Jimenez, M. A. Biopolymers 2010, 94, 779–790.
25. Makwana, K. M.; Mahalakshmi, R. Org Biomol Chem 2014, 12, 2053–2061.
26. Makwana, K. M.; Mahalakshmi, R. Phys Chem Chem Phys 2015, 17, 4220–4230.
27. Makwana, K. M.; Mahalakshmi, R. ChemBioChem 2014, 15, 2357–2360.
28. Honda, S.; Kobayashi, N.; Munekata, E. J Mol Biol 2000, 295, 269–278.
29. Mahalakshmi, R.; Raghothama, S.; Balaram, P. J Am Chem Soc 2006, 128, 1125–1138.
30. Wu, L.; McElheny, D.; Takekiyo, T.; Keiderling, T. A. Biochemistry 2010, 49, 4705–4714.
31. Makwana, K. M.; Raghothama, S.; Mahalakshmi, R. Phys Chem Chem Phys 2013, 15, 15321–15324.
32. Riemen, A. J.; Waters, M. L. Biopolymers 2008, 90, 394–398.
33. Eidenschink, L.; Crabbe, E.; Andersen, N. H. Biopolymers 2009, 91, 557–564.
34. Kier, B. L.; Shu, I.; Eidenschink, L. A.; Andersen, N. H. Proc Natl Acad Sci USA 2010, 107, 10466–10471.
35. Anderson, J. M.; Kier, B. L.; Shcherbakov, A. A.; Andersen, N. H. FEBS Lett 2014, 588, 4749–4753.
36. Tugyi, R.; Uray, K.; Ivan, D.; Fellinger, E.; Perkins, A.; Hudecz, F. Proc Natl Acad Sci USA 2005, 102, 413–418.
37. Towse, C. L.; Hopping, G.; Vulovic, I.; Daggett, V. Protein Eng Des Sel 2014, 27, 447–455.
38. Sievers, S. A.; Karanicolas, J.; Chang, H. W.; Zhao, A.; Jiang, L.; Zirafi, O.; Stevens, J. T.; Munch, J.; Baker, D.; Eisenberg, D. Nature 2011, 475, 96. U117.