Novel Gly building units for backbone cyclization: synthesis and incorporation into model peptides.
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.
Gazal
Sharon
S
Department of Organic Chemistry, Hebrew University of Jerusalem, Jerusalem 91904, Israel.
Gellerman
Gary
G
Gilon
Chaim
C
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
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010456:Peptides, Cyclic; D005998:Glycine