Round 8: 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. (10[2])Derivatives (-5[1])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 (10[1])carbodiimides (“carbo-die-IM-mydes”) in Merrifield solid-phase synthesis. In that method, these compounds must be protected by groups like Boc (“bock”) and Fmoc (10[2])(“F-mock”). These compounds are formed (-5[1])by treating an aldehyde with hydrogen cyanide then hydrolysis during the Strecker synthesis. (10[1])Simple examples of these (-5[1])compounds can be formed by electrical discharges, as demonstrated by Miller and Urey. (-5[1])For 10 points, (10[2])name these building blocks for polypeptides. (10[1])■END■ (10[3])

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