The CBS catalyst is derived from this molecule, which, along with its hydroxy-derivative and glycine, stabilizes the triple helix.
An equimolar mixture of this molecule and borane in THF can reduce ketones to secondary alcohols by forming oxazaborolidine in situ. In DMF, this molecule reacts with an enolate to form an intermediate that attacks only the re-face of an electrophilic aldehyde, while in a selectively-syn reaction, a PMP-protected imine reacts with an enamine formed from this molecule to create a betaamino- carbonyl. This common asymmetric organocatalyst allows ligands to bind to (*) SH3 domains and forms bonds that exhibit cis-trans isomerism. Zinc acts as a competitive inhibitor of this molecule's iron-dependent gamma-hydroxylation, which also requires an ascorbate cofactor. The CBS catalyst is derived from this molecule, which, along with its hydroxy-derivative and glycine, stabilizes the triple helix. For 10 points, name this amino acid that turns yellow in the ninhydrin test due to its pyrrolidine side chain, abundant in collagen.
An equimolar mixture of this molecule and borane in THF can reduce ketones to secondary alcohols by forming oxazaborolidine in situ.
R- or S- or D- or L-proline [accept Pro or P; accept pyrrolidine-2-carboxylic acid; accept CBS catalyst or Corey-Bakshi-Shibata catalyst or (R)-2-methyl-CBS-oxazaborolidine before "oxazaborolidine"]