The Synthesis Of Palmitoyl Pentapetide-3Intermediate

Palmitoyl pentapetide-3is a product which is polymerized by the end ofcollagen-I pieces and palmitic acid. It boosts radiance of complexion, helps restorefirmness, increases moisture and elasticity, improves skin firmness and reduces finelines by stimulating the synthesis of collagen, hyaluronic acid and elastin. Palmitoylpentapetide-3is a new generation of cosmetics additives that many problemsoccurring in skin can be prevented and it can improve skin at the beginning. In orderto meet the growing demand for whitening and skin care, the synthetic technologywhich suited for its industrialized production was researched, and it has profoundsignificance for replacing imported products, improving people’s quality of life andlight industry’s development.The palmitoyl pentapetide-3intermediate was synthesized from palmitic acid,L-Threonine, L-Serine and Cbz-Lysine by amino or carboxyl group protected,amidation, deprotection and so on. Palmitoyl dipeptide and Cbz-Lys-Ser dipeptidewith respective productivity of75%and65%were synthetized at low temp and roomtemp with piecewise technique, in which, methyl alcohol, tetrahydrofuran ordichloromethane as solvent, EDCI and HOBt were used as condensing agent, DIPEAas alkali. Pentapeptide which was obtained by recrystallization from dichloromethanein about34%total-yield was synthetized by acylation with DMF as solvents, and themethyl groups were took off from ester by hydrolysis under alkaline conditions.Organic synthesis is an important way of gaining short peptide, and there aremany ways to protect amino and carboxyl group. In this article, we employed the Bocto protect amino and then removed by HCl(g); and the carbomethoxy to protectcarboxyl and then removed by hydrolyzing with alcoholic solution of NaOH or KOH.In order to obtain the ultimate product with a high purification, each intermediate wasisolated and purified in the liquid-phase synthesis process. We have discussed andresolved many major issues in the organic synthesis process. Most of the intermediateshave not literature data to follow, and almost every reaction was isolated and purifiedby washing and recrystallization. The structure of compounds was also identified bythe methods of IR and NMR. In addition, we made a detailed introduction for reactionconditions and methods, and the related spectra and data were discussed and analyzeddeeply.