A simple one-step procedure is found to be highly effective for the "functionalization" of glycodiversity. This study encompasses 50 unprotected mono- and oligosaccharides, which are subjected to Kochetkov aminations in saturated aqueous ammonium carbonate. The reaction allows for the stereo- and regioselective introduction of an amino group into all oligosaccharides tested, as well as into a great variety of monosaccharides including charged species. The resulting unprotected glycosylamines are stable compounds, and the inherent amino group provides a convenient site for chemoselective conjugation and modification as described in the following paper in this issue.
lo] In analogous investigations of the interaction of barbituric acid with other compounds capable of forming hydrogen hond?. for example urea and 2aminopyrirnidine. 1 ' 1 aggregates were not found. In these cases all the bands of free barbituric acid appeared in addition to heak bands resulting from complex formation. 1111 The isotherm of lipid 3 shows that it has a collapse area of ca. 38 A' per molecule. Above 23°C the lipid forms a liquid-solid coexistence region, below 23 C only a gas phase and a solid-analogous phase are observed. The U V W s spectra were measured on the monolayer at a subphase temperature of 25°C and a surface pressure of ca. 5 m N m I .[12] Detailed investigations of the cleavagc by a retro-Knoevenagel reaction on the lipid monoiayer and their influence on the aqueous plrdse through aggregates will be reported separately (J. An,. Chem. So<.. submitted).(131 Note added in proof (December I , 1994): An X-ray structure determination carried out in the meantime by Dr. Dieter Schollmeyer, lnstitut fur Organische Chemie der Universitit Mainr, shows that by the incorporation of water molecules the individual components of the system 1.2 in the structure are linked to give a network by ionic and hydrogen bonds.
Chemical genomics aim to create synergy between synthetic small molecule chemistry and biosciences employing genomic tools and information. Central to chemical genomics is the discovery of bioactive compounds from novel targets for pharmaceutical lead development. The field is challenged both by the multitude and novelty of protein and other biomacromolecular targets to be studied. Affinity fingerprints, data sets of binding interactions between collections of chemicals and their macromolecular receptors, hold promise to guide drug design and study protein function for groups of related compounds and families of biomacromolecules. Despite their fundamental relevance, neither experimental protocols nor databases of quantitative and comprehensive description of binding interactions for small molecule ligands and biomacromolecular receptors are available. Chemical microarrays in combination with label-free imaging provide a novel route towards the systematic and standardized acquisition and application of such affinity fingerprint information.
Glycosylamines are readily available carbohydrate derivatives that undergo acylation reactions with homobifunctional N-hydroxysuccinimidyl esters. The product glycosylamides carry a spacer group equipped with one active ester functionality. This route provides well-defined glycoconjugates, which may be cross-linked to various amino-functionalized resins. Carbohydrate recognition of the resulting sugar-bead conjugates is probed by lectin immunostaining or flow cytometry using a fluorescently labeled lectin.
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