Reactive intermediates in peptide synthesis. ortho-Nitrophenyl Nalpha-para-toluenesulfonyl-alpha-aminoisobutyrate.
The preparation, characterization, and molecular and crystal structures of the title compound [IUPAC name: 2-nitrophenyl 2-methyl-2-(para-toluenesulfonylamino)propanoate], C(17)H(18)N(2)O(6)S, are reported. The phenyl group is almost perpendicular to the plane of the adjacent ester moiety. One O atom of the nitro group is wedged between the two ester O atoms. The implications of this peculiar conformation for the chemistry of ortho-nitrophenyl esters in peptide synthesis are discussed.
Crisma
Marco
M
Biopolymer Research Centre, CNR, Department of Organic Chemistry, University of Padova, Via Marzolo 1, 35131, Italy. marco.crisma@unipd.it
Toniolo
Claudio
C
D000621:Aminoisobutyric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis*
D000621:Aminoisobutyric Acids; D007202:Indicators and Reagents; D010455:Peptides; C459721:nitrophenyl N-oluenesulfonyl-aminoisobutyrate