Multicentered hydrogen bonding in 1-[(1-de-oxy-β-d-fructo-pyranos-1-yl)aza-nium-yl]cyclo-pentane-carboxyl-ate ('d-fructose-cyclo-leucine').

ABSTRACT: The title compound, C₁₂H₂₁NO₇, (I), is conformationally unstable; the predominant form present in its solution is the β-pyran-ose form (74.3%), followed by the β- and α-furan-oses (12.1 and 10.2%, respectively), α-pyran-ose (3.4%), and traces of the acyclic carbohydrate tautomer. In the crystalline state, the carbohydrate part of (I) adopts the ² C ₅ β-pyran-ose conformation, and the amino acid portion exists as a zwitterion, with the side chain cyclo-pentane ring assuming the E ₉ envelope conformation. All heteroatoms are involved in hydrogen bonding that forms a system of anti-parallel infinite chains of fused R ₃ ³(6) and R ₃ ³(8) rings.

SUBMITTER: Mossine VV 

PROVIDER: S-EPMC6690447 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature