Round 9: Tossup 6

TOAC (“T-O-A-C”) is a cyclic, radical one of these compounds used as a spin label in EPR spectroscopy. Isotope-labeled versions of these compounds are used in SILAC (“SYE-lack”) experiments. Derivatives of one of these compounds react with boroxines (“bor-OCK-seens”) to form asymmetric Corey–Bakshi–Shibata catalysts. These compounds are conjugated onto Wang resins using coupling agents (10[1])like benzotriazoles or carbodiimides (10[1])(“carbo-die-IM-mydes”) in Merrifield solid-phase (10[1])synthesis. In that method, these compounds must be protected by groups like Boc (“bock”) and Fmoc (“F-mock”). These compounds are formed by treating an aldehyde with hydrogen cyanide then hydrolysis during the Strecker synthesis. (10[1])Simple (10[1])examples of these compounds can be formed by electrical discharges, as demonstrated by Miller and Urey. For 10 points, name these building blocks (10[1])for polypeptides. (10[1])■END■ (10[1])

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