Synthesis and Use of Tetrahydrofuran- and Tetrahydropyran-Amino Acids

Abstract

Abstract. Progress in the synthesis and the use of amino acids containing a THF or THP ring is reported. Different synthetic routes from carbohydrates or α-amino acids as starting compounds are discussed. Examples for THF-and THP-

Carbohydrate-Based Mimetics in Drug Design: Sugar Amino Acids and Carbohydrate Scaffolds

“…We use the term “sugar amino acid”, SAA, as a functional, succinct classification term, although a plethora of terms have been proposed in the literature for compounds derived from SAAs. These include saccharide-peptide hybrids, glycosamino acids and glycotides, peptidosaccharides, saccharopeptides, − amide-linked carbohydrates, tetrahydrofuran-(pyran) amino acids, − and carbopeptoids, − although the latter compounds most often do not have a peptoid functionality (IUPAC definition). The term saccharopeptides has also been used to describe oligosaccharides in which the glycosidic linkage has been replaced by an amide bond. , Some publications use the term “sugar amino acids” for glycosylated amino acids, , for a disaccharide based on an amino- and carboxyl cyclopropyl-carbohydrate derivative, or in one case even for conjugates based on the Michael addition of C-terminally protected amino acids to 2,3-dideoxy-hex-2-enopyranos-4-uloses …”

Folding Propensity of Cyclohexylether-δ-peptides

“…It was reasoned that breaking the symmetry and repetitiveness of individual oligomers might not only result in more disperse NMR signals but moreover lead to materials with local orientation and ultimately better folding properties. We decided to explore C-2 substitution, as present in the THF and THP amino acids . Initial attempts to alkylate monomer 3 led to unseparable mixtures.…”