Sarin is an acid fluoride and ester of methylphosphonic acid.

Sarin is a deadly nerve gas that was outlawed by the Chemical Weapons Convention of 1993. However, it has been used at various times as a weapon of mass destruction by terrorists, including a 1995 attack in the Tokyo metro and a 2013 attack by the Syrian government on rebel forces during the Syrian civil war.

(a) Sarin is chiral; the S enantiomer is more active than the R enantiomer. Draw a line-and-wedge structure of the more active enantiomer.

(b) Sarin’s biological effects are due to its reaction with a serine residue in the active site of acetylcholinesterase, an enzyme that is very important in nerve transmission.

Give the product of the reaction of the more active enantiomer of sarin with serine.

Transcribed Image Text:

O O-P-CH3 F sarin (propan-2-yl methylphosphonofluoridate)