Solid-Phase synthesis of a dendritic peptide related to a retinoblastoma protein fragment utilizing a combined boc- and fmoc-chemistry approach.
Dendritic peptides, often presented as multiple antigen peptides (MAPs), are widely used in immunological-based fields of research, although their synthesis can be extremely challenging. In this paper, a tetrameric dendritic MAP-like presentation of the retinoblastoma protein [649-654] sequence (4RB(649-654)) has been prepared using solid-phase peptide synthesis (SPPS) methods. During the synthesis of this dendritic molecule, numerous modifications to the synthetic protocols were examined. These modifications included the introduction of a combination Boc- and Fmoc-chemistry approach and also the use of 1,8-diazabicyclo[5.4.0]-undec-7-ene as a Fmoc-deprotection agent. The use in combination of Boc- and Fmoc-based synthetic strategies resulted in the production of the desired peptide molecule, 4RB(649-654), in high purity and acceptable yields following purification by reversed phase HPLC.
Cavallaro
V
V
Centre for Bioprocess Technology, Department of Biochemistry and Molecular Biology, Monash University, Clayton, Australia.
Thompson
P
P
Hearn
M
M
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry*; D002621:Chemistry / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D003712:Dendrites / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry*; D008969:Molecular Sequence Data; D010452:Peptide Biosynthesis; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D016160:Retinoblastoma Protein / Q000737:chemistry*; D013997:Time Factors; D014269:Trifluoroacetic Acid / Q000737:chemistry
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D016160:Retinoblastoma Protein; D014269:Trifluoroacetic Acid