Citation: Xue-Yi Sun, Yulong Zhong, Yao-Hua Li, Daniel P. Miller, Sagar Buttan, Xiang-Xiang Wu, Yukun Zhang, Quan Tang, Hong-Wei Tan, Jin Zhu, Rui Liu, Eva Zurek, Zhong-Lin Lu, Bing Gong. Reliable folding of hybrid tetrapeptides into short β-hairpins[J]. Chinese Chemical Letters, ;2022, 33(1): 257-261. doi: 10.1016/j.cclet.2021.06.019 shu

Reliable folding of hybrid tetrapeptides into short β-hairpins

Xue-Yi Sun ^{a, 1} ,
Yulong Zhong ^{b, 1} ,
Yao-Hua Li ^a ,
Daniel P. Miller ^c ,
Sagar Buttan ^c ,
Xiang-Xiang Wu ^d ,
Yukun Zhang ^e ,
Quan Tang ^a ,
Hong-Wei Tan ^a ,
Jin Zhu ^e ,
Rui Liu ^a ,
Eva Zurek ^b ,
Zhong-Lin Lu ^{a, *} ,
Bing Gong ^{b, *}

a.
College of Chemistry, Beijing Normal University, Beijing 100875, China
b.
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260, United States
c.
Department of Chemistry, Hofstra University, Hempstead, NY 11549, United States
d.
Academy of Chinese Medical Science, Henan University of Chinese Medicine, Zhengzhou 450046, China
e.
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China

luzl@bnu.edu.cn

bgong@buffalo.edu

Received Date: 16 March 2021
Revised Date: 5 June 2021
Accepted Date: 7 June 2021
Available Online: 15 June 2021

Figures(6)

Five hybrid tetrapeptides, each consisting a central dipeptide segment of α-amino acid residues flanked by two aromatic γ-amino acid residues, are found to fold into well-defined β-hairpin conformations as shown by NMR, computational study, and X-ray structures. The turn loop of this β-hairpin motif accommodates different two-residue α-amino acid sequences from the highly flexible Gly-Gly, to the more restricted d-Pro-Gly. The presence of α-amino acid side chains enhances the stabilities of the β-hairpins with the exception of d-Pro-Gly-which results in destabilization. Based on this hairpin/turn motif, a variety of different dipeptide sequences of α-amino acids which rarely occur in β-turns can be introduced and presented as two-residue loops.
- β-Hairpin,
- β-Turn,
- γ-Amino acid,
- NMR,
- X-ray
1. [1]
  P.N. Lewis, F.A. Momany, H.A. Scheraga, BBA-Protein Struct 303(1973) 211-229. doi: 10.1016/0005-2795(73)90350-4
2. [2]
  G.D. Rose, L.M. Glerasch, J.A. Smith, Adv. Protein Chem. 37(1985) 1-109. doi: 10.1039/d0sc03060k
3. [3]
  C.M. Wilmot, J.M. Thornton, J. Mol. Biol. 203(1988) 221-232. doi: 10.1016/0022-2836(88)90103-9
4. [4]
  E.G. Hutchinson, J.M. Thornton, Protein Sci. 3(1994) 2207-2216. doi: 10.1002/pro.5560031206
5. [5]
  B. Madan, S.Y. Seo, S.G. Lee, Proteins 82(2014) 1721-1733. doi: 10.1002/prot.24526
6. [6]
  T.S. Haque, J.S. Little, S.H. Gellman, J. Am. Chem. Soc. 118(1996) 6975-6985. doi: 10.1021/ja960429j
7. [7]
  T.S. Haque, S.H. Gellman, J. Am. Chem. Soc. 119(1997) 2303-2304. doi: 10.1021/ja963653h
8. [8]
  J.F. Espinosa, S.H. Gellman, Angew. Chem. Int. Ed. 39(2000) 2330-2333. doi: 10.1002/1521-3773(20000703)39:13<2330::AID-ANIE2330>3.0.CO;2-C
9. [9]
  F.A. Syud, H.E. Stanger, S.H. Gellman, J. Am. Chem. Soc. 123(2001) 8667-8677. doi: 10.1021/ja0109803
10. [10]
  E. de Alba, M.A. Jiménez, M. Rico, J. Am. Chem. Soc. 119(1997) 175-183. doi: 10.1021/ja962325e
11. [11]
  A.J. Maynard, M.S. Searle, Chem. Commun. (1997) 1297-1298. doi: 10.1007/978-1-4939-1486-9_2
12. [12]
  E.R. Simpson, J.K. Meldrum, R. Bofill, et al., Angew. Chem. Int. Ed. 44(2005) 4939-4944. doi: 10.1002/anie.200500577
13. [13]
  S. Aravinda, N. Shamala, R. Rajkishore, et al., Angew. Chem. Int. Ed. Engl. 41(2002) 3863-3865. doi: 10.1002/1521-3773(20021018)41:20<3863::AID-ANIE3863>3.0.CO;2-A
14. [14]
  N. Tonali, I. Correia, J. Lesma, et al., Org. Biomol. Chem. 18(2020) 3452-3458. doi: 10.1039/C9OB02654A
15. [15]
  A.M.C. Marcelino, L.M. Gierasch, Biopolymers 89(2008) 380-391. doi: 10.1002/bip.20960
16. [16]
  D. Du, Y. Zhu, C.Y. Huang, et al., Proc. Natl. Acad. Sci. U. S. A. 101(2004) 15915-15920. doi: 10.1073/pnas.0405904101
17. [17]
  J.D.A. Tyndall, B. Pfeiffer, G. Abbenante, et al., Chem. Rev. 105(2005) 793-826. doi: 10.1021/cr040689g
18. [18]
  W.L. DeLano, M.H. Ultsch, A.M. de Vos, et al., Science 287(2000) 1279-1283. doi: 10.1126/science.287.5456.1279
19. [19]
  Y. Jiang, H. Long, Y. Zhu, Y. Zeng, Chin. Chem. Lett. 29(2018) 1067-1073. doi: 10.1016/j.cclet.2018.05.028
20. [20]
  P. Yang, C. Yang, K. Zhang, et al., Chin. Chem. Lett. 29(2018) 1181-1184. doi: 10.1016/j.cclet.2018.01.045
21. [21]
  R.T. Shukla, Y.U. Sasidhar, Proteins 83(2015) 1352-1367. doi: 10.1002/prot.24831
22. [22]
  I.L. Batalha, I. Lychko, R.J.F. Branco, O. Iranzo, A.C.A. Roque, Org. Biomol. Chem. 17(2019) 3996-4004. doi: 10.1039/C9OB00564A
23. [23]
  Y.G. Shi, Y.F. Wang, L. Jayaraman, et al., Cell 94(1998) 585-594. doi: 10.1016/S0092-8674(00)81600-1
24. [24]
  R.P. Leon, M. Tecklenburg, R.A. Sclafani, Genetics 179(2008) 1757-1768. doi: 10.1534/genetics.108.088690
25. [25]
  M.L. Li, D.R. Zhou, H. Zhao, et al., Chin. Chem. Lett. 20(2009) 1315-1318. doi: 10.1016/j.cclet.2009.06.008
26. [26]
  J.S. Nowick, D.L. Holmes, G. Mackin, et al., J. Am. Chem. Soc. 118(1996) 2764-2765. doi: 10.1021/ja953334a
27. [27]
  H.Q. Zeng, X.W. Yang, R.A. Flowers, et al., J. Am. Chem. Soc. 124(2002) 2903-2910. doi: 10.1021/ja010701b
28. [28]
  L. Sebaoun, V. Maurizot, T. Granier, et al., J. Am. Chem. Soc. 136(2014) 2168-2174. doi: 10.1021/ja412729s
29. [29]
  J.E. Ross, P.C. Knipe, S. Thompson, et al., Chem. Eur. J. 21(2015) 13518-13521. doi: 10.1002/chem.201502690
30. [30]
  B. Gole, B. Kauffmann, V. Maurizot, et al., Angew. Chem. Int. Ed. 58(2019) 8063-8067. doi: 10.1002/anie.201902378
31. [31]
  J.D. Pham, N. Chim, C.W. Goulding, et al., J. Am. Chem. Soc. 135(2013) 12460-12468. doi: 10.1021/ja4068854
32. [32]
  D. Seebach, S. Abele, K. Gademann, et al., Angew. Chem. Int. Ed. 38(1999) 1595-1597. doi: 10.1002/(SICI)1521-3773(19990601)38:11<1595::AID-ANIE1595>3.0.CO;2-0
33. [33]
  X. Daura, K. Gademann, H. Schäfer, et al., J. Am. Chem. Soc. 123(2001) 2393-2404. doi: 10.1021/ja003689g
34. [34]
  S. Chatterjee, P.G. Vasudev, S. Raghothama, et al., J. Am. Chem. Soc. 131(2009) 5956-5965. doi: 10.1021/ja900618h
35. [35]
  B. Gong, Acc. Chem. Res. 45(2012) 2077-2087. doi: 10.1021/ar300007k
36. [36]
  B. Gong, Y. Yan, H. Zeng, et al., J. Am. Chem. Soc. 121(1999) 5607-5608. doi: 10.1021/ja990904o
37. [37]
  Y.D. Shi, Q. Tang, Y.F. Jiang, et al., Chem. Commun. 54(2018) 3719-3722. doi: 10.1039/C8CC01564C
38. [38]
  Y.K. Zhang, R.K. Cao, J. Shen, et al., Org. Lett. 20(2018) 1555-1558. doi: 10.1021/acs.orglett.8b00283
39. [39]
  Y.K. Zhang, Y.L. Zhong, A.L. Connor, et al., J. Am. Chem. Soc. 141(2019) 14239-14248. doi: 10.1021/jacs.9b06094
40. [40]
  Q. Tang, Y.L. Zhong, D.P. Miller, et al., Org. Lett. 22(2020) 1003-1007. doi: 10.1021/acs.orglett.9b04547
41. [41]
  Y.L. Zhong, Q. Tang, D.P. Miller, et al., Front. Chem. 8(2020) 530083. doi: 10.3389/fchem.2020.530083
42. [42]
  G. te Velde, F.M. Bickelhaupt, E.J. Baerends, et al., J. Comput. Chem. 22(2001) 931-967. doi: 10.1002/jcc.1056
43. [43]
  G. Kresse, J. Furthmuller, Phys. Rev. B 54(1996) 11179-11186. doi: 10.1103/PhysRevB.54.11169
44. [44]
  S. Grimme, J. Antony, S. Ehrlich, et al., J. Chem. Phys. 132(2010) 154104. doi: 10.1063/1.3382344
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