Comparison of the effects of 5- and 6-HOAt on model peptide coupling reactions relative to the cases for the 4- and 7-Isomers.
Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.
Department of Chemistry, University of Massachusetts, Amherst, Massachusetts 01003, USA. carpino@chem.umass.edu
L A
LA
Carpino
H
H
Imazumi
B M
BM
Foxman
M J
MJ
Vela
P
P
Henklein
A
A
El-Faham
J
J
Klose
M
M
Bienert
D000814:Aniline Compounds / Q000378:metabolism; D007536:Isomerism; D007700:Kinetics; D008745:Methylation; D009584:Nitrogen / Q000378:metabolism; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism*; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*
D000814:Aniline Compounds; D010455:Peptides; D014230:Triazoles; C011852:1-hydroxybenzotriazole; D009584:Nitrogen; C004658:4-chloroaniline