941292-83-7Relevant academic research and scientific papers
Differential Effects of β3- versus β2-Amino Acid Residues on the Helicity and Recognition Properties of Bim BH3-Derived α/β-Peptides
Eddinger, Geoffrey A.,Gellman, Samuel H.
supporting information, p. 13829 - 13832 (2018/09/25)
Oligomers containing α- and β-amino acid residues (α/β-peptides) have been shown to mimic the α-helical conformation of conventional peptides when the unnatural residues are derived from β3-amino acids or cyclic β-amino acids, but the impact of incorporating β2 residues has received little attention. The effects of β2 residues on the conformation and recognition behavior of α/β-peptides that mimic an isolated α-helix were investigated. This effort has focused on 26-mers based on the Bim BH3 domain; a set of isomers with identical α/β backbones that differ only in the placement of certain side chains along the backbone (β3 vs. β2 substitution) was compared. Circular dichroism data suggest that β2 residues can be helix-destabilizing relative to β3 residues, although the size of this effect seems to depend on side chain identity. Binding data show that β3→β2 substitution at sites that contact a partner protein, Bcl-xL, can influence affinity in a way that transcends effects on helicity.
Practical synthesis of enantiomerically pure β2-amino acids via proline-catalyzed diastereoselective aminomethylation of aldehydes
Chi, Yonggui,English, Emily P.,Pomerantz, William C.,Horne, W. Seth,Joyce, Leo A.,Alexander, Lane R.,Fleming, William S.,Hopkins, Elizabeth A.,Gellman, Samuel H.
, p. 6050 - 6055 (2008/02/08)
Proline-catalyzed diastereoselective aminomethylation of aldehydes using a chiral iminium ion, generated from a readily prepared precursor, provides α-substituted-β-amino aldehydes with 85:15 to 90: 10 dr. The α-substituted-β-amino aldehydes can be reduce
CONCISE BETA2-AMINO ACID SYNTHESIS VIA ORGANOCATALYTIC AMINOMETHYLATION
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Page/Page column 14; 32; 39; 41; 45, (2010/11/28)
The present invention provides a method for the synthesis of ?2-amino acids. The method also provides methods yielding a-substituted ?-amino aldehydes and ?-substituted γ-amino alcohols. The present method according to this invention allows for increased yield and easier purification using minimal chromatography or crystallization. The methods described herein are based on an aldehyde aminomethylation which involves a Mannich reaction between an aldehyde and a formaldehyde-derived N,O-acetal (iminium precursor) and a catalyst, such as, for example, L-proline or a pyrrolidine. The invention allows for large scale, commercial preparation of ?2-amino acids.
