16356-05-1Relevant articles and documents
Reeve,Reichel
, p. 68 (1972)
β-turn and β-hairpin mimicry with tetrasubstituted alkenes
Gardner, Robb R.,Liang, Gui-Bai,Gellman, Samuel H.
, p. 1806 - 1816 (1999)
Synthesis and conformational analysis are reported for molecules containing the trans-5-amino-3,4-dimethylpent-3-enoic acid residue (ADPA, 1). This amino acid is a glycylglycine mimic, in which the central amide group is replaced with an E-tetrasubstituted alkene. It was anticipated that this isosteric replacement would promote specific local (β-turn) and nonlocal (β-hairpin) conformational preferences. Previous work has shown that the most common β-turn conformations (type I and type II) are not strong inducers of β-hairpin formation, while the rare 'mirror image' β-turns (type I' and type II') promote β-hairpin formation. We therefore sought an achiral unit with a strong turn-forming propensity, since the lack of stereogenic centers within such a unit would eliminate the energetic distinction between common and 'mirror image' turn conformations. In, the ADPA unit, avoidance of allylic strain was expected to preorganize the backbone for adoption of folded conformations. A combination of NMR and IR data for di-, tri-, and tetrapeptide analogues containing the ADPA residue reveal that β-turn- and β-hairpin-like folding is promoted in methylene chloride solution.
IMIDAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
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, (2008/06/13)
The present invention provides a novel imidazole derivative having the chemical formula STR1 These compounds are useful for preventing or treating hypertension or congestive heart failure and have high activity, rapid action upon intravenous injection, go
Reactions of 2,3-Dimethylenebutadiene Dianion with Electrophiles. Synthesis and Conformations of 2,3-Disubstituted-1,3-butadienes
Bates, Robert B.,Gordon, Bernard,Highsmith, Thomas K.,White, James J.
, p. 2981 - 2987 (2007/10/02)
Reactions of 2,3-dimethylenebutadiene dianion 1 with monofunctional electrophiles were found to provide the best routes to symmetrically substituted 1,3-butadienes such as 2c - n.Evidence that at least some of these reactions go by single electron-transfer mechanisms is presented.Possible mechanisms for the formation of some unusual byproducts are discussed.Reactions of 1 with dichlorides and dibromides were found to provide the best routes to most 1,2-dimethylenecycloalkanes 3, the corresponding dimers 4 and trimers 5, and 1,1-dimethyl-3,4-dimethylene-1-metallacyclopentanes 26.From their UV spectra, the dienes 2 contain about 60percent transoid conformations, except 2,3-dimethyl-1,3-butadiene (2a) which shows about 100percent and 2,3-dineopentyl-1,3-butadiene (2h) which shows about 30percent. 1,2-Dimethylenecycloalkanes 3 display cisoid conformations in rings smaller than 9-membered and transoid conformations in rings larger than 11.When the ring size exceeds 15, the homoallylic methylene groups on both sides are also anti coplanar.With rings larger than about 30, the next methylene group on each side is also anti coplanar, and when the ring size exceeds about 45, an additional methylene on each side is anti coplanar.