Solid State and Solution Conformation of 6-[4-[N-tert-ButoxycarbonylN-(N′-ethyl)propanamide]imidazolyl]-6-deoxycyclomaltoheptaose: Evidence of Self-Inclusion of the Boc Group within the β-Cyclodextrin Cavity

✍ Scribed by Giuseppe Impellizzeri; Giuseppe Pappalardo; Franca D'Alessandro; Enrico Rizzarelli; Michele Saviano; Rosa Iacovino; Ettore Benedetti; Carlo Pedone

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 559 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(200003)2000:6<1065::aid-ejoc1065>3.0.co;2-i

✦ Synopsis

A new modified β-cyclodextrin (β-CD) derivative 1 that was functionalized in position 6 with Boc-Carcinine was synthesised and its crystal structure was determined. The structure reveals a ''sleeping swan''-like shape, the covalently bonded Boc-Carcinine moiety forming a folded structure with the Boc group inserted within the hydrophobic cavity of the β-cyclodextrin. The conformation of the Carcinine moiety is determined by the inclusion of the Boc group and is further stabilised by three intramolecular hydrogen bonds, two between the amide N1-H group, the carbonyl CЈ1=O1 group and a primary hydroxylic group of the glucose unit 5, one between the carbonyl CЈ0=O0 group and the primary hydroxylic group of the glucose unit 2. The β-CD macrocycle