19462-08-9Relevant academic research and scientific papers
COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
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Page/Page column 45-49; 53, (2010/12/31)
The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.
Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans
Sun, Ping,Wang, Chunlei,Breitbach, Zachary S.,Zhang, Ying,Armstrong, Daniel W.
experimental part, p. 10215 - 10226 (2010/05/01)
An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic-and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromaticfunctionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high "loadability" and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.
The Resolution and Absolute Configuration by X-Ray Crystallography of the Isomeric Octopamines and Synephrines
Midgley, John M.,Thonoor, Mohan C.,Drake, Alex F.,Williams, Clyde M.,Koziol, Anna E.,Palenik, Gus J.
, p. 963 - 970 (2007/10/02)
Racemates of the naturally occuring biogenic amines, o-, m-, and p-octopamine and p-synephrine, have been resolved by the preparation of suitable diastereomeric salts with antipodes of appropriate organic acids.The circular dichroism (c.d.) curves of (-)-m-octopamine hydrochloride and (-)-m-synephrine hydrochloride were superimposable and of opposite sign to those of the corresponding (-)-p-derivatives.X-ray crystallography of the (-)-3-bromocamphor-8-sulphonate salt of (-)-p-synephrine confirmed (for the first time by direct means in this series of compounds) that the absolute configuration of (-)-p-synephrine is R.It is concluded from the c.d. data that the absolute configuration of (-)-p-octopamine is also R.
