Tetrahedron p. 9823 - 9834 (1996)
Update date:2022-07-29
Topics:
Ranganathan, Subramania
Tamilarasu, Natarajan
Roy, Raja
The cysteine capped, ends protected cross linked motifs 6 and 7, arising from pairs of proximally placed cysteines wherein within a 22 atom framework are inscribed 3 disulphide bridges and 2 peptide linkage, have been prepared and their conformations derived by detailed 1H NMR studies and molecular modeling protocols, where excellent agreement was seen. Both compounds 6 and 7 possess a C2 symmetric hydrogen bonded pair involving the peptide NH and the CO of the proximate N-protecting group (Boc or Z). The nature of the latter profoundly influences the conformation. Thus, in 6 where the unit is Boc a bend conformation was promoted by hydrophobic interactions; alternatively in 7 with a Z-protecting group the conformation was linear. Compounds 6 and 7 have much promise in diverse aspects of protein design.
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