title: Novel Gly building units for backbone cyclization: synthesis and incorporation into model peptides.
abstract: We report the preparation of novel building units for backbone cyclization that have the general formula Fmoc-Nalpha[CH(R)CO2Al]Gly-OH. These building units were prepared by the reductive alkylation method using allyl esters of several amino acids as starting material and hence, respectively, contain the side chain of these amino acids. These N-alkylated Gly building units were incorporated in model backbone cyclic peptides. The resulting crude backbone cyclic peptides were obtained in high degree of purity according to HPLC and mass spectrometric analyses.
authors.affiliation: Department of Organic Chemistry, Hebrew University of Jerusalem, Jerusalem 91904, Israel.
authors.forename: Sharon
authors.initials: S
authors.lastname: Gazal
authors.forename: Gary
authors.initials: G
authors.lastname: Gellerman
authors.forename: Chaim
authors.initials: C
authors.lastname: Gilon
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry; D003500:Cyclization; D005449:Fluorenes / Q000737:chemistry; D005998:Glycine / Q000737:chemistry*; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010456:Peptides, Cyclic; D005998:Glycine