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Stereochemistry and Isomerism (5B) Practice Test

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Q1

A peptide-mimetic inhibitor, Molecule K, contains two stereocenters and is synthesized as four stereoisomers. Only K(2R,3S) shows potent inhibition of a chiral protease. The lab isolates K(2R,3S) and K(2S,3R) and notes they have identical melting points and equal-magnitude opposite-sign optical rotations, but sharply different inhibition constants are not observed between these two. Which statement best describes the stereochemical relationship between K(2R,3S) and K(2S,3R) consistent with the physical data?

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