125679-71-2Relevant academic research and scientific papers
Native Serine Peptide Assembly – Scope and Utility
Pirrung, Michael C.,Schreihans, Ryan S.
, p. 5633 - 5636 (2016)
This work develops serine peptide assembly (SPA), which complements and contrasts with classic native chemical ligation (NCL). Advances in reagentless peptide-bond formation have been applied to serine (and serine models) and a range of C-terminal amino acids, including bulky residues that are not amenable to NCL. The particular appeal of SPA is preparative-scale segment condensations with zero racemization risk and favorable process mass intensity (PMI). Mechanistic studies support a previously proposed reaction pathway via an initial transesterification step. An understanding of the factors favoring this pathway relies on hard–soft acid–base theory, according to which mildly activated esters with the largest carbonyl positive charge are most reactive with hydroxyamines. Novel C-terminal activators have been discovered that enhance reactivity and give harmless byproducts.
A novel, simple and rapid protocol for N-protected-oxazolidine-5-ones
Reddy, G. Vidyasagar,Rao, G. Venkat,Iyengar
, p. 4071 - 4077 (2007/10/03)
A simple and efficient method for the preparation of N-protected oxazolidine-5-ones using microwave irradiation is described.
A New Approach for Chiral Allyl Amines via a Novel Dichloromethylenation of Oxazolidinones
Reddy, G. Vidyasagar,Iyengar, D. S.
, p. 1237 - 1238 (2007/10/03)
A novel dichloromethylenation of oxazolidinones and their conversion to allyl amines 3a-e, key precursors for potential HIV protease inhibitors is described.
