Ranganathan, S. ; Venkateshwarlu, P. ; Babu, S. M. ; Reddy, N. S. ; Basha, S. J. ; Sarma, A. V. S. ; Vijay, D. ; Sastry, G. N. (2010) Triply bridged (1,3,5) cyclophanes from cystine and lanthionine linkers- a comparison Tetrahedron, 66 (22). 3923-3929 . ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tet.2010.03.091
Abstract
The condensation of benzene 1,3,5-tricarbonylchloride with cystine-di-Me [H2N-CH(COOMe)-CH2-S-S-CH2-CH(COOMe)-NH2] yielded triply bridged (1,3,5) cyclophane 1, which was shown by detailed spectral studies and molecular orbital calculations to have a D3 symmetry with conformationally identical linkers and a spherical topology. In sharp contrast, the (1,3,5) cyclophane 2 from the rarely studied lanthionine di-Me [H2N-CH(COOMe)-CH2-S-CH2-CH(COOMe)-NH2], showed only a equatorial twofold symmetry. This work highlights the special properties of the -S-S- bridge in cystine, which makes it an exceptional synthon in nature and organic synthesis.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Cystine(-S-S-) Linker; Rigid; Stable; Lanthionine (-S-) Linker Flexible |
| ID Code: | 48838 |
| Deposited On: | 20 Jul 2011 06:54 |
| Last Modified: | 20 Jul 2011 08:33 |
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