Rigid-Rodβ-Barrels as Lipocalin Models: Probing Confined Space by Carotenoid Encapsulation
摘要:
Herein, we describe the design, synthesis, structure, and function of synthetic, supramolecular beta-barrel models. Assembly of octi(p-phenylene)s with complementary -Lys-Leu-Lys-NH2 and Glu-Leu-Glu-NH2 side chains yielded water-soluble rigid-rod beta-barrels of precise length and with flexible diameter. A hydrophobic interior was evidenced by guest encapsulation. Host-guest complexes with planarized, monomeric beta-carotene within tetrameric rigid-rod beta-barrels, and disc micellar astaxanthin J-aggregates surrounded by about dodecameric rigid-rod "bicycle tires" were prepared from mixed micelles by dialytic detergent removal. The significance of these findings for future bioorganic chemistry in confined, intratoroidal space is discussed in comparison with pertinent biological examples.
Rigid-Rodβ-Barrels as Lipocalin Models: Probing Confined Space by Carotenoid Encapsulation
摘要:
Herein, we describe the design, synthesis, structure, and function of synthetic, supramolecular beta-barrel models. Assembly of octi(p-phenylene)s with complementary -Lys-Leu-Lys-NH2 and Glu-Leu-Glu-NH2 side chains yielded water-soluble rigid-rod beta-barrels of precise length and with flexible diameter. A hydrophobic interior was evidenced by guest encapsulation. Host-guest complexes with planarized, monomeric beta-carotene within tetrameric rigid-rod beta-barrels, and disc micellar astaxanthin J-aggregates surrounded by about dodecameric rigid-rod "bicycle tires" were prepared from mixed micelles by dialytic detergent removal. The significance of these findings for future bioorganic chemistry in confined, intratoroidal space is discussed in comparison with pertinent biological examples.
2-Amino-4-pyrrolidinothieno[2,3-<i>d</i>]pyrimidine-6-carboxylic Acid as an<i>N</i>-Terminal Surrogate in Amino Acid and Peptide Analogues
作者:George Varvounis、Paul Cordopatis、Evangelos E. Bissyris、Dimitris Belekos、Vassiliki Magafa、Petros G. Tsoungas
DOI:10.1055/s-2005-918426
日期:——
(ATPC) is an unnatural amino acid with promise in applications as a building block for the synthesis of peptidomimetics. ATPC was obtained from both 3a and 3b thienopyrimidines by hydrolysis and hydrogenolysis, respectively. The synthesis of eleven ATPC-amino acids and two ATPC-peptides is described. ATPC is incorporated as N-terminal moiety in solution or solid-phase peptide synthesis using Boc or