Round 7: 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 like benzotriazoles or carbodiimides (“carbo-die-IM-mydes”) in Merrifield solid-phase synthesis. In that method, these compounds (10[1])must be protected by groups like Boc (“bock”) and Fmoc (10[1])(“F-mock”). These compounds are formed by treating an aldehyde with hydrogen cyanide then hydrolysis during the Strecker synthesis. (-5[1])Simple examples of these compounds can be formed by electrical discharges, as demonstrated by Miller and Urey. For 10 points, name these building blocks for polypeptides. ■END■ (10[2])

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