Cyclic homooligomers from sugar amino acids: synthesis, conformational analysis, and significance.
Sugar amino acids (SAAs) were designed as new building blocks carrying an amino group and a carboxyl group on a carbohydrate scaffold. By exploiting standard solid- and solution-phase coupling procedures, linear and cyclic homooligomers containing glucosyluronic acid methylamine (Gum) were synthesized. We achieved a high yield and a very short coupling time for the oligomerization and cyclization of sequences encompassing two, three, four, and six Gum units. The synthesis of cyclic oligomers containing only SAAs as repetitive units has not been reported before. The conformational preferences in aqueous solution of the cyclic derivatives and their applications as potential host molecules are described herein. Benzoic acid and p-nitrophenol were chosen as model guest molecules to study the formation of cyclodextrin-like inclusion complexes. The complexation behavior of the cyclic hexamer was proved from three different points of view: chemical shifts, longitudinal relaxations (T(1)), and diffusion coefficients. All of them showed different values for host and guest molecules measured independently and in the presence of each other.
Locardi
E
E
Institut für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.
Stöckle
M
M
Gruner
S
S
Kessler
H
H
D000596:Amino Acids / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry; D002236:Carbohydrate Conformation; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D009596:Nitrophenols / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility
D000596:Amino Acids; D009596:Nitrophenols; D009844:Oligosaccharides; D019817:Benzoic Acid; D005947:Glucose; C024836:4-nitrophenol