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- W1996137497 abstract "The Nepsilon-fumaroylated diketopiperazine of L-Lys (FDKP, 1) self-assembles into microparticles that can be used for pulmonary drug delivery. When these particles are formulated with insulin, the resultant powder (Technosphere Insulin) provides a novel prandial insulin therapy. To better understand the self-assembly of 1, a series of model compounds were synthesized that allowed for the determination of the preferred intramolecular hydrogen-bonding pattern of FDKP. Variable-temperature NMR (CDCl3) and FTIR studies of acyclic diamides (3-7a) and diketopiperazine models (7b- 9d) revealed the preference of a 10-membered hydrogen bond between one of the diketopiperazine's amido NH and the appended fumaramido-carbonyl (assigned as a type B H bond). Molecular modeling studies identified a low energy conformer in the architecture of 1, which contains two Nepsilon-fumaroylated lysine side chains appended to the diketopiperazine core. The lowest energy form involved a cooperative hydrogen bond motif which involved only one of the diketopiperazine amides and had one arm involved in a type B motif and the other in a type A hydrogen bond (i.e., the fumaramidyl NH H-bonding to the diketopiperazine amide carbonyl). This cooperative hydrogen bond scenario orients the appended fumaryl groups into a distinctive 90 degrees arrangement and is likely involved in its self-assembly into microparticles." @default.
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- W1996137497 date "2008-02-07" @default.
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- W1996137497 title "A Delineation of Diketopiperazine Self-Assembly Processes: Understanding the Molecular Events Involved in <i>N</i><sup>ϵ</sup>-(Fumaroyl)diketopiperazine of <scp>l</scp>-Lys (FDKP) Interactions" @default.
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- W1996137497 doi "https://doi.org/10.1021/mp700096e" @default.
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