Design of a depside with a lipophilic adamantane moiety: Synthesis, crystal structure and molecular conformation

Journal of Molecular Structure

Volumn 832, Issue 1-3, 2007, Pages 191-198

  Matković, Marija ^a   Veljković, Jelena ^a   Mlinarić Majerski, Kata ^a   Molčanov, Krešimir ^a   Kojić Prodić, Biserka ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Adamantyl hydroxybutanoic acid; Conformation; Depside design; X ray structure analysis

Indexed keywords

CONFORMATIONS; CRYSTAL STRUCTURE; HYDROGEN BONDS; MOLECULAR DYNAMICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ADAMANTYL HYDROXYBUTANOIC ACID; DEPSIDE DESIGN; X-RAY STRUCTURE ANALYSIS;

PARAFFINS;

EID: 33847648779     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2006.08.022     Document Type: Article

References (29)

1. Filip S.V., and Cavelier F. J. Pept. Sci. 10 (2004) 115-118
2. Davies J.S., Howe J., Jayatilake J., and Riley T. Lett. Pept. Sci. 4 (1997) 441-445
3. Dawson J.R., Dory Y.L., Mellor J.M., and McAleer J.F. Tetrahedron 52 (1996) 1361-1378
4. Kuisle O., Quiñoá E., and Riguera R. J. Org. Chem. 64 (1999) 8063-8075
5. Dory Y.L., Mellor J.M., and McAleer J.F. Tetrahedron 52 (1996) 1343-1360
6. For a review of synthesis of cyclic peptides and depsides see:. Davies J.S. J. Pept. Sci. 9 (2003) 471-501
7. For the construction of cyclic peptides with conformationally rigid alicyclic (1,3-adamantanedicarbonyl or 2,3-norbornenedicarbonyl) units, see:. Ranganathan D., Haridas V., Nagaraj R., and Karle I.L. J. Org. Chem. 65 (2000) 4415-4422 and references cited therein
8. Horvat S., Mlinarić-Majerski K., Glavaš-Obrovac Lj., Jakas A., Veljković J., Marczi S., Kragol G., Roščić M., Matković M., and Milostić-Srb A. J. Med. Chem. 49 (2006) 3136-3142
9. Govender T., Hariprakasha H.K., Kruger H.G., and Raasch T. S. Afr. J. Chem. 58 (2005) 37-40
10. Govender T., Kruger H.G., and Raasch T. Struct. Chem. 16 (2005) 129-134
11. Pätzel M., Sanktjohanser M., Doss A., Henklein P., and Szeimies G. Eur. J. Org. Chem. (2004) 493-498
12. Park K.-H., and Kurth M.J. Tetrahedron 58 (2002) 8629-8659
13. Gonzalez A., Marquet J., and Moreno-Mañas M. Tetrahedron 42 (1986) 4253-4257
14. Wünsch E., Heindrich H.G., and Grassmann W. Chem. Ber. 97 (1964) 1818-1828
15. Note 12 in the reference:. Sasaki T., Shimizu K., and Ohno M. Chem. Pharm. Bull. 32 (1984) 1433-1440
16. K. Harms, S. Wocadlo, XCAD-4 Program for Processing CAD4 Diffractometer Data, 1995, University of Marburg, Germany.
17. Farrugia L.J. J. Appl. Crystallogr. 32 (1999) 837-838
18. G.M. Sheldrick, SHELXL97 Program for the Refinement of Crystal Structures, 1997, Universität Göttingen, Germany.
19. Spek T. PLATON98: A Multipurpose Crystallographic Tool, 120398 Version (1998), University of Utrecht, Utrecht, The Netherlands
20. Farrugia L.J. ORTEP-3 for Windows. J. Appl. Crystallogr. 30 (1997) 565
21. Bruno I.J., Cole J.C., Edgington P.R., Kessler M.K., Macrae C.F., McCabe P., Pearson J., and Taylor R. Acta Crystallogr. B 58 (2002) 389-397
22. Rostkowska H., Nowak M.J., Lapinski L., and Adamowicz L. Phys. Chem. Chem. Phys. 3 (2001) 3012-3017
23. Došlić N., and Kühn O. Z. Phys. Chem. 217 (2003) 1507-1524
24. Olah G.A., Narang S.C., Gupta B.G.B., and Malhotra R. J. Org. Chem. 44 (1979) 1247-1251
25. Silverstein R.M., and Webster F.X. Spectrometric Identification of Organic Compounds. sixth ed. (1998), John Wiley & Sons Inc., New York
26. Pretsch E., Clerc T., Seibl J., and Simon W. Tabellen zur Strukturaufklärung Organischer Verbindungen mit Spektroskopischen Methoden (1981), Springer Verlag, Berlin
27. D = +25 ± 1 (c = 1, EtOH)}, we suppose that the small amount of (R)-Boc-PheOH was present and therefore an adequate amount of racemic 1a and 1b was formed. However, we cannot exclude the partial racemisation during the synthesis of 1a and 1b.
28. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), IUCr, Oxford, UK
29. Jeffrey G.A. An Introduction to Hydrogen Bonding (1997), Oxford University Press, Oxford