Synthesis of a cyclic analogue of the C-loop region of epidermal growth factor, containing 1-aminocyclopropane-1-carboxylic acid.
We report the synthesis of a cyclic analogue of epidermal growth factor sequence 33-42 with substitution of 1-aminocyclopropane-1-carboxylic acid for glycine at position 39 (N-acetyl-Cys-Val-Ile-Gly-Tyr-Ser-ACPCA-Asp-Arg-Cys-NH2). The analogue was synthesised by solid-phase methods, using t-Boc chemistry and acid-labile side-chain protecting groups. The use of the 4-methoxybenzyl protecting group for C- and N-terminal cysteine residues resulted in the spontaneous formation of the desired intramolecular disulfide bond after HF deprotection.
Bailie
J R
JR
School of Biology and Biochemistry, Queen's University of Belfast, Division of Biochemistry, Northern Ireland, UK.
Walker
B
B
Nelson
J
J
Murphy
R F
RF
D000595:Amino Acid Sequence; D003515:Cycloleucine / Q000737:chemistry*; D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry; D004815:Epidermal Growth Factor / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000138:chemical synthesis; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D011487:Protein Conformation; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
D004220:Disulfides; D010446:Peptide Fragments; D010456:Peptides, Cyclic; D013438:Sulfhydryl Compounds; D003515:Cycloleucine; D004815:Epidermal Growth Factor