Advertisement

Structural Chemistry

, Volume 23, Issue 3, pp 873–877 | Cite as

A theoretical reappraisal of the cyclol hypothesis

  • Ibon Alkorta
  • Goar Sánchez-Sanz
  • Cristina Trujillo
  • Luis Miguel Azofra
  • José Elguero
Original Research
First Online:

Abstract

Theoretical calculations at the B3LYP/6-31G(d) level have been carried out on the isomerization of cyclic-tri-glycine into the corresponding tri-cyclol. The results confirmed that the cyclol hypothesis was untenable both from a thermodynamic as well as from a kinetic point of view.

Keywords

Peptides Cyclol Green fluorescent protein B3LYP/6-31G(d) Energy profile 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgments

We thank the Ministerio de Ciencia e Innovación (Project No. CTQ2009-13129-C02-02) and the Comunidad Autónoma de Madrid (Project MADRISOLAR2, ref. S2009/PPQ-1533) for continuing support. Thanks are given to the CTI (CSIC) for an allocation of computer time.

References

  1. 1.
    Wrinch D (1937) Nature 139:972–973CrossRefGoogle Scholar
  2. 2.
    Wrinch D (1937) Proc Royal Soc London Series A Math Phys Sci 161:505–524CrossRefGoogle Scholar
  3. 3.
    Wrinch D (1940) Nature 145:669–670CrossRefGoogle Scholar
  4. 4.
    Bernal JD (1939) Nature 143:74–75CrossRefGoogle Scholar
  5. 5.
    Bernal JD (1939) Nature 143:663–667CrossRefGoogle Scholar
  6. 6.
    Bernal JD, Fankuchen I, Riley D (1939) Nature 143:897CrossRefGoogle Scholar
  7. 7.
    Pauling L, Niemann LC (1939) J Am Chem Soc 61:1860–1867CrossRefGoogle Scholar
  8. 8.
    Jones DS, Kenner GW, Sheppard RC (1963) Experientia 19:126–127CrossRefGoogle Scholar
  9. 9.
    Glover GI, Rapoport H (1964) J Am Chem Soc 86:3397–3398CrossRefGoogle Scholar
  10. 10.
    Shemyakin MM, Antonov VK, Shkrob AM, Shchelokov VI, Agadzhanyan ZE (1965) Tetrahedron 21:3537–3572CrossRefGoogle Scholar
  11. 11.
    Wakamiya T, Shiba T, Kaneko T, Sakakibara H, Noda T, Take T (1973) Bull Chem Soc Jap 46:949–954CrossRefGoogle Scholar
  12. 12.
    Lucente G, Pinnen F, Romeo A, Zanotti G (1983) J Chem Soc Perkin Trans 1:1127–1130CrossRefGoogle Scholar
  13. 13.
    Zanotti G, Pinnen F, Lucente G, Cerrini S, Gavazzo E, Mazza F (1983) Int J Pept Protein Res 22:410–421CrossRefGoogle Scholar
  14. 14.
    Maier W, Luthra R, Gröger D (1989) J Basic Microbiol 29:483–490CrossRefGoogle Scholar
  15. 15.
    Rajappa S, Natekar MV (1993) Piperizine-2,5-diones and related lactim ethers. Adv Heterocycl Chem 57:187–289 (see page 211)CrossRefGoogle Scholar
  16. 16.
    Guedez T, Núñez A, Tineo E, Núñez O (2002) J Chem Soc Perkin Trans 2:2078–2082Google Scholar
  17. 17.
    García Borboa L, Núñez O (2006) J Phys Org Chem 19:737–743CrossRefGoogle Scholar
  18. 18.
    Contreras-Torres FF, Basiuk VA (2006) J Phys Chem A 110:7431–7440CrossRefGoogle Scholar
  19. 19.
    Bethencourt L, Núñez O (2008) J Org Chem 73:2105–2113CrossRefGoogle Scholar
  20. 20.
    Tsien RY (1998) Ann Rev Biochem 67:509–544CrossRefGoogle Scholar
  21. 21.
  22. 22.
    Gaussian 09 (2009), Revision A.1, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr., JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian, Inc., WallingfordGoogle Scholar
  23. 23.
    Becke AD (1988) Phys Rev A 38:3098–3100CrossRefGoogle Scholar
  24. 24.
    Becke AD (1993) J Chem Phys 98:5648–5652CrossRefGoogle Scholar
  25. 25.
    Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789CrossRefGoogle Scholar
  26. 26.
    Hariharan PA, Pople JA (1973) Theor Chim Acta 28:213–222CrossRefGoogle Scholar
  27. 27.
    McIver JW, Komornicki AK (1972) J Am Chem Soc 94:2625–2633CrossRefGoogle Scholar
  28. 28.
    Rothe M, Steffen KD, Rothe I (1965) Angew Chem Int Ed 4:356Google Scholar
  29. 29.
    Manjula G, Ramakrishnan C, Sarathy KP (1977) Proc Indian Acad Sci 86:443–454Google Scholar
  30. 30.
    Jeremic T, Linden A, Moehle K, Heimgartner H (2005) Tetrahedron 61:871–883CrossRefGoogle Scholar
  31. 31.
    Umezawa K, Ikeda Y, Uchihata Y, Naganawa H, Kondo S (2000) J Org Chem 65:459–463CrossRefGoogle Scholar
  32. 32.
    Oelke AJ, Antonietti F, Bertone L, Cranwell PB, France DJ, Goss JMR, Hofmann T, Knauer S, Moss SJ, Skelton PC, Turner RM, Wuitschik G, Ley SV (2011) Chem Eur J 17:4183–4194CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Ibon Alkorta
    • 1
  • Goar Sánchez-Sanz
    • 1
  • Cristina Trujillo
    • 1
  • Luis Miguel Azofra
    • 1
  • José Elguero
    • 1
  1. 1.Instituto de Química Médica (C.S.I.C.)MadridSpain

Personalised recommendations

Cite article

Buy options