Die konkurrierende 1,2‐ und 1,3‐Acylwanderung. Zur Kenntnis des 2‐Oxy‐3,4‐diamino‐pentans. II. Teil¹)

Abstract

Reversible 1,2 and 1,3 acyl migrations with retention of configuration are shown to occur in 2‐hydroxy‐3,4‐diamino‐pentane. In 2‐hydroxy‐3,4‐bis(acetylamino)‐pentane, where 1,2 and 1,3 migration of like acyl groupe compete, the former reaction was the only one observed. In 2‐hydroxy‐3‐benzoylamino‐4‐acetylamino‐pentane, where 1,2 benzoyl migration competes with 1,3 acetyl migration, the latter predominated.

Synthesis of the Succinic Ester of Homoserine, a New Intermediate in the Bacterial Biosynthesis of Methionine*

“…The rate factor of 25 between O-succinylhomoserine and O-acetylserine is consistent with previous results showing that, with S-acetyl thiolesters, S->-N 1,2-acyl transfer occurred sixty times faster than 1,3 (Wieland and Hornig, 1956). Preferential 1,2 over 1,3 transfer has also been shown for oxygen esters (Grob and Wagner, 1955). The eight times greater rate for O-acetylthreonine over O-acetylserine is contrary to the expected effects of alkyl substitution on a bimolecular reaction between an amine and an ester (Gould, 1959).…”