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Aziridine (You're strainin' my nitrogen)

By moleculeoftheday on July 5, 2007.

Aziridine, like cyclopropane and oxiranes/epoxides, is one of the simple strained three-membered rings. The strain imparts considerable reactivity.

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Aziridine is kind of neat - like many crazy reactive moieties, it's attracted attention for use in cancer drugs. It's also one of my favorite big strong organiker reagents that finds its way into the biology lab. A cysteine residue in a protein (R-CH2-SH) will react with an aziridine to make R-CH2-S-CH2-CH2-NH3+ (Cf. lysine, which it mimics, R-CH2-CH2-CH2-CH2-NH3+). Never done this reaction, but apparently the superlative nucleophilicity of sulfur is such that the reaction is essentially completely selective.

Cysteine to lysine, just add aziridine!

I would love to hear from anyone who has attempted (succeeded?) at this derivatization.

Tags
Synthesis

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