Studies on a new immunoactive peptide, FK-156. IV. Synthesis of FK-156 and its geometric isomer.
For the structural confirmation of FK-156, two possible structures, 1 and its geometric isomer 2, were synthesized. Di-Z-meso-diaminopimelic acid (4) was converted into 14 via a sequence of reactions involving, as key steps, an enzyme-mediated asymmetric hydrolysis (6 leads to 7), followed by carbobenzyloxylation using a copper chelate procedure (7 leads to 8). Condensation of 14 and the appropriately protected lactoyl dipeptide 17 and removal of the protecting groups of the resulting 18 afforded 1. Protection of 7 to 22, followed by coupling to glycine via an azide method, gave 25. Derivatization of 25 to 29 and condensation with 17 gave 30, which was deprotected to yield 2. Compound 1 proved to be identical in all respects with the natural product.
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis*; D000599:Amino Acids, Diamino / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003960:Diaminopimelic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000276:Adjuvants, Immunologic; D000599:Amino Acids, Diamino; D003960:Diaminopimelic Acid; C034330:FK 156