Chemical Synthesis and Characterization of Skin Care Peptides
Disciplines
Biochemistry | Medicinal-Pharmaceutical Chemistry
Abstract (300 words maximum)
Peptides have gained a lot of attention in skin care products because of their beneficial properties and cost efficiency. Overall, peptides are known for their multifaceted properties to help with anti-aging properties. Although most of the natural peptides are extracted from various biological sources, the purity and quality of these peptides are questionable. Besides extracting these peptides, the specific skin care peptide can also be synthesized by traditional solid phase peptide synthesis protocols, however, very few studies are reported. The goal of this research is to synthesize skin-care peptide using solid phase peptide synthesis and characterize them by mass spectrometry to confirm the synthesis and purity. Two peptides were synthesized using the Blue Liberty microwave peptide synthesizer with the help of Rink amide resin. In the first step, the 9-fluorenylmethoxycarbonyl (Fmoc) group was removed from amino acids using piperidine, and then coupling was performed by activator (diisopropylcarbodiimide) and activator bases (oxyma). The couplings and deprotection steps are repeated for each amino acid. Subsequently, the peptide-resin was dried using DCM. The peptide was cleaved from the resin using a cleavage cocktail containing 95% TFA, 2.5% TIPS and 2.5% water. This helps separate the peptide chain from the resin. Then, Nitrogen gas assisted to remove any remaining TFA. Afterwards, the cold ether was added to precipitate the peptide, and 10% acetic acid was mixed to dissolve the peptide and subsequently froze and lyophilize overnight. This study shows that the peptide was successfully synthesized as evident of two peaks observed at m/z 564.3 and 282.67 which correspond to [M+H]+ and [M+2H]2+ charge states matched with the theoretical mass of the peptide. The second peptide was also synthesized but the mass spectrum showed that one arginine residue is missing from the intact peptide. In future, the toxicity of these peptides will be investigated.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Mohammad A. Halim
Chemical Synthesis and Characterization of Skin Care Peptides
Peptides have gained a lot of attention in skin care products because of their beneficial properties and cost efficiency. Overall, peptides are known for their multifaceted properties to help with anti-aging properties. Although most of the natural peptides are extracted from various biological sources, the purity and quality of these peptides are questionable. Besides extracting these peptides, the specific skin care peptide can also be synthesized by traditional solid phase peptide synthesis protocols, however, very few studies are reported. The goal of this research is to synthesize skin-care peptide using solid phase peptide synthesis and characterize them by mass spectrometry to confirm the synthesis and purity. Two peptides were synthesized using the Blue Liberty microwave peptide synthesizer with the help of Rink amide resin. In the first step, the 9-fluorenylmethoxycarbonyl (Fmoc) group was removed from amino acids using piperidine, and then coupling was performed by activator (diisopropylcarbodiimide) and activator bases (oxyma). The couplings and deprotection steps are repeated for each amino acid. Subsequently, the peptide-resin was dried using DCM. The peptide was cleaved from the resin using a cleavage cocktail containing 95% TFA, 2.5% TIPS and 2.5% water. This helps separate the peptide chain from the resin. Then, Nitrogen gas assisted to remove any remaining TFA. Afterwards, the cold ether was added to precipitate the peptide, and 10% acetic acid was mixed to dissolve the peptide and subsequently froze and lyophilize overnight. This study shows that the peptide was successfully synthesized as evident of two peaks observed at m/z 564.3 and 282.67 which correspond to [M+H]+ and [M+2H]2+ charge states matched with the theoretical mass of the peptide. The second peptide was also synthesized but the mass spectrum showed that one arginine residue is missing from the intact peptide. In future, the toxicity of these peptides will be investigated.