| pubmed-article:20376829 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:20376829 | lifeskim:mentions | umls-concept:C0011953 | lld:lifeskim |
| pubmed-article:20376829 | pubmed:issue | 17 | lld:pubmed |
| pubmed-article:20376829 | pubmed:dateCreated | 2010-4-28 | lld:pubmed |
| pubmed-article:20376829 | pubmed:abstractText | Solvent-dependent, self-discrimination of diamides is described. Mixing a solution of (R)-1a and (S)-1a, which are valine-derived, bis(2-hydroxyphenyl)diamide-bearing, multiple hydrogen-bonding modules, in dichloromethane immediately led to the formation of a thick suspension comprising a 1:1 heterochiral aggregate of 1a. The solubility of heterochiral 1a was substantially lower in halogenated solvents than in ethyl acetate. A perusal of racemic crystal structures obtained from chloroform and ethyl acetate revealed a significant difference in the crystal-packing pattern, which is likely to be the basis for the pronounced difference in solubility. Specific self-discrimination of 1 a in an ensemble of eight structurally related molecules showcased the specific aggregation through the hydrogen-bonding network of the bis(2-hydroxyphenyl)diamide framework. The low solubility of heterochiral 1a in halogenated solvent was exploited to achieve high stereoselectivity in a catalytic asymmetric reaction by using a low enantiomeric excess sample of 1a. | lld:pubmed |
| pubmed-article:20376829 | pubmed:language | eng | lld:pubmed |
| pubmed-article:20376829 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:20376829 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:20376829 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:20376829 | pubmed:month | May | lld:pubmed |
| pubmed-article:20376829 | pubmed:issn | 1521-3765 | lld:pubmed |
| pubmed-article:20376829 | pubmed:author | pubmed-author:ShibasakiMasa... | lld:pubmed |
| pubmed-article:20376829 | pubmed:author | pubmed-author:KumagaiNaoyaN | lld:pubmed |
| pubmed-article:20376829 | pubmed:author | pubmed-author:NojiriAkihiro... | lld:pubmed |
| pubmed-article:20376829 | pubmed:author | pubmed-author:MatsuzawaAkin... | lld:pubmed |
| pubmed-article:20376829 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:20376829 | pubmed:day | 3 | lld:pubmed |
| pubmed-article:20376829 | pubmed:volume | 16 | lld:pubmed |
| pubmed-article:20376829 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:20376829 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:20376829 | pubmed:pagination | 5036-42 | lld:pubmed |
| pubmed-article:20376829 | pubmed:meshHeading | pubmed-meshheading:20376829... | lld:pubmed |
| pubmed-article:20376829 | pubmed:meshHeading | pubmed-meshheading:20376829... | lld:pubmed |
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| pubmed-article:20376829 | pubmed:meshHeading | pubmed-meshheading:20376829... | lld:pubmed |
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| pubmed-article:20376829 | pubmed:meshHeading | pubmed-meshheading:20376829... | lld:pubmed |
| pubmed-article:20376829 | pubmed:meshHeading | pubmed-meshheading:20376829... | lld:pubmed |
| pubmed-article:20376829 | pubmed:meshHeading | pubmed-meshheading:20376829... | lld:pubmed |
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| pubmed-article:20376829 | pubmed:meshHeading | pubmed-meshheading:20376829... | lld:pubmed |
| pubmed-article:20376829 | pubmed:year | 2010 | lld:pubmed |
| pubmed-article:20376829 | pubmed:articleTitle | Solvent-dependent self-discrimination of bis(2-hydroxyphenyl)diamides. | lld:pubmed |
| pubmed-article:20376829 | pubmed:affiliation | Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. | lld:pubmed |
| pubmed-article:20376829 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:20376829 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
