Carboxylic acid complexation by a synthetic analog of the "carboxylate-binding pocket" of vancomycin

Cavity Effects on the Enantioselectivity of Chiral Amido[4]resorcinarene Stereoisomers

“…Enzyme catalysis plays a crucial role in all biochemical processes. Natural and artificial enzymes normally exhibit a high enantioselectivity toward chiral molecules as a consequence of shape‐specific noncovalent attractive and repulsive intermolecular interactions 1–5. An important step toward the elucidation of enzyme mechanisms requires a comprehensive kinetic study using simplified models under conditions, such as the gas phase, where the molecule/receptor interactions are not perturbed by medium effects 6…”

An approach to a synthetic carboxylate-binding pocket based on β-avoparcin

“…The N-Acyloxazolidinone 12. "-To a solution of the carboxylic acid 10 (2.46 g, 5.56 mmol) in diethyl ether (26 cm3) was added triethylamine (0.80 cm', 5.73 mmol). The mixture was stirred at 0 "C while trimethylacetyl chloride (0.71 cm3, 5.73 mmol) was added dropwise (a white precipitate formed), and the mixture was stirred at 0 "C for 2 h. In a separate flask, to a cooled ( -78 "C) solution of (I?…”

Antibacterial glycopeptide antibiotics (review)

“…As the methods of cyclization developed, syntheses of ever more complex model glycopeptide systems were realized. Thus, a method was developed for the synthesis of the model 16-membered M(4-O-6) glycopeptide ring [25], the bicyclic M(2-0-4)(4-0-6) fragment of vancomycin was synthesized [22], and a series of other compounds were obtained [26,27]. A significant contribution in this region was made by the discovery by Yamamura's group of an elegant method involving the oxidation of aryl rings each having one hydroxyl and two halogen substituents by thaUium(III) nitrate.…”