Lactose analogues

Recombinant resilin production was induced, with the nonmetabolizable lactose analogue IPTG, in the Escherichia coli bacterial strain BL21(DE3)/pLysS. Cells were collected by centrifugation (10,000 g, 20 min at 4°C) and the cell pellet frozen at 80°C. 

The second family of A-linked oligosaccharides are called the lactosamine family in which the D-mannose residues of the core pentasaccharide are substituted 1 2 by lactosamine, which is a lactose analogue with A-acetyl-D-glucosamine substituted for D-glucopyranose at the reducing-end of lactose. The lactosamine is frequently substituted by A-acetyl-D-neu-raminic acid (for the structure of A-acetyl-D-neuraminic acid, see the monomer residue in colominic acid,0 Sect. 8.2 andO Fig. 7) linked 2 3 or 2 6 [142,143]. The third family has a mixed structure of the high mannose and lactosamine families [144,145,146,147]. 

The solution conformations of the C-linked lactose analogues 32-34, and in particular the flexibility of the interglycosidic linkages, have been examined by NMR spectroscopy, as well as computational methods. Compound 32 is very similar to natural lactose around the glycosidic bond but more flexible about the aglyconic bond. Analogue 33 is similar to 32, its isomer 34, however, is more... 

Physical studies on glycosides have included the X-ray diffraction analysis of methyl a-D-galactopyranosides and methyl p-D-glucopyranosides with fatty acid esters at C-6 which showed bilayer structures with zig-zag alkyl chains. The conformational behaviour of several non-ionisable lactose analogues have been examined by NMR and molecular mechanics methods, and the energy profile of methyl p-D-arabinofuranoside as a function of ring conformations has been determined by gas phase computations. ... 

Hydroxypyridonimine analogues (177) of the much-studied 3-hydroxy-4-pyridinones (cf. Section 5.4.5.5.2), are prepared from maltose or lactose. They form stable iron(III) complexes. 

R. G. Edwards, L. Hough, and A. C. Richardson, Transformations of cellobiose derivatives into analogues of lactose, Carbohydr. Res., 55 (1977) 129-148. 

Nitroglycerin (correctly termed glyceryl trinitrate) is the most successful analogue of organic nitrates (Fig. 10.2). The compound is a triester formed by the nitration of glycerol (1,2,3-propanetriol), and was discovered by Sobrero in 1847 [14]. In pure form, nitroglycerin is an explosive, as was discovered by Alfred Nobel, but when combined with an inert carrier (such as lactose) it is stable enough to be... 

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