Microwave-assisted synthesis of triple-helical, collagen-mimetic lipopeptides.
Collagen-mimetic peptides and lipopeptides are widely used as substrates for matrix degrading enzymes, as new biomaterials for tissue engineering, as drug delivery systems and so on. However, the preparation and subsequent purification of these peptides and their fatty-acid conjugates are really challenging. Herein, we report a rapid microwave-assisted, solid-phase synthetic protocol to prepare the fatty-acid conjugated, triple-helical peptides containing the cleavage site for the enzyme matrix metalloproteinase-9 (MMP-9). We employed a PEG-based resin as the solid support and the amino acids were protected with Fmoc- and tert-butyl groups. The amino acids were coupled at 50 degrees C (25 W of microwave power) for 5 min. The deprotection reactions were carried out at 75 degrees C (35 W of microwave power) for 3 min. Using this protocol, a peptide containing 23 amino acids was synthesized and then conjugated to stearic acid in 14 h.
Banerjee
Jayati
J
Department of Pharmaceutical Sciences, North Dakota State University, Fargo, North Dakota, USA.
Hanson
Andrea J
AJ
Muhonen
Wallace W
WW
Shabb
John B
JB
Mallik
Sanku
S
D003094:Collagen / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D055666:Lipopeptides / Q000138:chemical synthesis*; D008872:Microwaves; D012984:Software; D014584:User-Computer Interface
D055666:Lipopeptides; D003094:Collagen