N-octyl-D-gluconamide

Fuhrhop and coworkers [54] discovered higher aggregates - ropes - consisting of quadruple helices of N-octyl-D-gluconamide 104. 

Figure 5.16 A) Solid state CPMAS- C-NMR spectra of crystalline and microcrystalline N-octyl-D-gluconamide (= d-GIu-8) materials are well-resolved. The signals have been assigned by considering gauche effects and by comparisons with solution state NMR spectra. The chemical shifts in the first spectrum correspond to an all-anti conformation, shifts in the second spectrum to a gauche bend (b). The methyl carbon C-8 signal indicates a polar environment oriented for the monolayer crystal a), and an unpolar environment for the bilayer crystal b) and micellar fibre c). The signals for the lyophilizedfibre in the third spectrum are somewhat broadened, but the shift of the C-2 signals can be clearly detected. This points to a G conformation (b).

The first chiral superstructures from /V,n-alkyl aldonamides were discovered when aqueous gels of A,n-octyl-D-gluconamide (D-Glu-8 or D-90a, concentration 1-50%) were prepared by dissolving this compound at high temperature and... 

Figure 4.5.8 (a) Transmission electron micrograph and (b) computer image of an N-octyl-D-gluconamide quadruple helical fiber. 

S. Khoshkhoo and J. Anwar. Study of the effect of solvent on the morphology of crystals using molecular simulation Application to a-resorcinol and iV-n-octyl-D-gluconamide. J. Chem. Soc., Faraday Trans. 92,1996, 1023. 

Morphologically diverse supramolecular assemblies have been formed from long-chain chiral aldonamides [370-378]. Typical compounds include 28 30. Formation of 200- and 300-A-diameter rods and helical rope-like structures in aqueous n-octyl- and n-dodecyl-D-gluconamide (D-28-8 and D-28-12) gpls has been recognized for some time [379]. In a subsequent work, helical double-... 

Figure 4.2.4 Crystal structure of (a) A -octyl-D-gluconamide (monolayer) and (b) N-octyl-D-gulonamide (bilayer). Compare with zig-zag conformation in Figure 4.2.1. (From Svenson et al., 1994a,b.)...

A C-n.mjr. study on the gelation of -octyl-D-gluconamide in aqueous solution has been published. ... 

The P-D-fructofuranosylamine-derived oxazolidinone 20 in the configuration, JV-(n-octyl)-6-deoxy-D-gluconamide, AT-(l-octyl)-D-arabinonamide, iV-(l-dodecyl)-D-ribonaniide, and the amide 21, the non-2-enoic acid ester 22 which is derived from a KDN derivative (see Chapter 16). ... 

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