Synthesis of fragments of transforming growth factor alpha incorporating exo-2-azabicyclo[2,2,1 ]heptane-3-carboxylic acids as proline substitutes

Article abstract of DOI:10.1016/00404-0399(50)1336-G

Two novel amino acids, the enantiomers ofexo 2-azabicyclo [2,2,1]heptane-3-carboxylic acid have been independent synthesized by the aza Diels Alder reaction using a chiral auxiliary. The two acids have been advanced via solid phase synthesis to afford linear sequences, which have been cyclized to afford cyclic disulfide peptides, analogues of fragments of TGFd. The structures of these and other fragments have been firmly established.