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Triply bridged (1,3,5) cyclophanes from cystine and lanthionine linkers—a comparison |
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| Authors: | S Ranganathan P Venkateshwarlu NS Reddy AVS Sarma |
| Institution: | a D-212, Discovery Laboratory, Organic Chemistry Division-III, Indian Institute of Chemical Technology, Hyderabad 500 607, India b Centre for NMR, Indian Institute of Chemical Technology, Hyderabad 500 607, India c Molecular Modeling Group, Organic Chemical Sciences, Indian Institute of Chemical Technology, Hyderabad 500 607, India |
| 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. |
| Keywords: | Cystine(-S-S-) linker Rigid Stable Lanthionine (-S-) linker flexible |
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