PubMed · 2201011
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W J Klish. 1990. Special infant formulas.. https://doi.org/10.1542/pir.12-2-55
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The synthesis and characterization of a new class of DOTA (1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane) monoamide-linked glycoconjugates (glucose, lactose and galactose) of different valencies (mono, di and tetra) and their Sm(III), Eu(III) and Gd(III) complexes are reported. The 1H NMR spectrum of Eu(III)-DOTALac2 shows the predominance of a single structural isomer of square antiprismatic geometry of the DOTA chelating moiety and fast rotation about the amide bond connected to the targeting glycodendrimer. The in vitro relaxivity of the Gd(III)-glycoconjugates was studied by 1H nuclear magnetic relaxation dispersion (NMRD), yielding parameters close to those reported for other DOTA monoamides. The known recognition of sugars by lectins makes these glycoconjugates good candidates for medical imaging agents (MRI and gamma scintigraphy).
Whereas C-2- and 4-ulopyranosyl compounds (C-2- and C-4-ulosides) can be converted to cyclopentenones under base conditions through beta-elimination and ring contraction, base-initiated beta-elimination of C-glycosyl 2'-aldehydes and 2'-ketones results in the formation of acyclic alpha,beta-unsaturated aldehydes or ketones. By combining both molecular features we synthesized 1-C-(4-ulopyranosyl)-2-oxoalkanes 6, 13, and 20 and investigated their reactions when they were treated with base. Both alpha- and beta-anomers of C-(4-ulopyranosyl)acetaldehydes 6 and 13 underwent a fast intramolecular aldol reaction between the C-5 enolate and 2'-aldehyde to form optically pure 8-oxabicyclo[3.2.1]octanones, which further transformed to 8-oxabicyclo[3.2.1]octenones 14 and 15 by beta-elimination. However, this aldol reaction did not occur when 1-C-(4-ulopyranosyl)propan-2-one 20 was treated with base because of steric hindrance exerted by the additional methyl group. Instead, an alternate C-3 enolization led to beta-elimination and further electro-ring opening to form an acyclic enol, which was then converted through a disrotatory intramolecular aldol cyclization to a cis-substituted cyclopentenone 21.
Complex fluids comprising of surfactants with water and/or oil form a rich variety of dynamic self-assembled structures, ranging from spherical swollen micelles, viscous rod-like micelles, and bicontinuous microemulsions to ordered liquid crystalline phases. The wide range of practical and specialized applications of complex fluids has made them the subject of intense research for many decades. Here, we demonstrate for the first time how bicontinuous microemulsions containing equal masses of oil and sugar can be driven to the glassy state without phase separation at ambient temperatures by controlled desiccation of sugar-rich microemulsions. The robust nanostructure of these microemulsion glasses allows polymerization of hydrophobic liquid monomers within the interstices of the glassy microemulsion template without macroscopic phase separation. Yet after polymerization, the sugar and surfactant template can be easily removed by dissolution in water.