Design and synthesis of beta-peptides with biological activity.
beta-Peptides have been used as a platform for developing bioactive compounds with various types of bioactivity such as antimicrobial activity, cholesterol absorption inhibition, somatostatin receptor agonist, and hDM2 inhibition. These bioactive beta-peptides have been designed based on bioactive alpha-peptides. Three main strategies have been used to design bioactive beta-peptides: direct conversion of alpha-peptide sequences into beta-peptide sequences, placement of side chains to provide desirable distribution of physicochemical properties, and the grafting of proteinaceous side chains critical for bioactivity onto beta-peptide structures. This chapter briefly discusses the various strategies employed to design bioactive beta-peptides, followed by protocols for the synthesis of N-alpha-fluorenylmethyloxycarbonyl (Fmoc)-protected beta3-amino acids from Fmoc-protected alpha-amino acids, and synthesis of beta-peptides by solid phase methods using Fmoc-based chemistry.
Koyack
Marc J
MJ
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY, USA.
Cheng
Richard P
RP
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry*; D006801:Humans; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D015202:Protein Engineering / Q000379:methods; D017433:Protein Structure, Secondary; D051736:Proto-Oncogene Proteins c-mdm2 / Q000037:antagonists & inhibitors; D011986:Receptors, Somatotropin / Q000037:antagonists & inhibitors
D000596:Amino Acids; D000890:Anti-Infective Agents; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D011986:Receptors, Somatotropin; C497206:MDM2 protein, human; D051736:Proto-Oncogene Proteins c-mdm2