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Rapid and Selective Cleavage of Amide Groups at Neutral pH: Applications from Hyaluronic Acid to Small Molecules
Author(s) -
Jing Jing,
Bankefors Johan,
Bonneaud Céline,
Sawen Elin,
Gerfaud Thibaud,
Westin Jonatan,
ElBazbouz Ghizlane,
Kandelin Lina,
Rousseau Antoine,
Olsson Johan,
Karlsson Anders,
Nord Lars,
BouixPeter Claire,
Helander Kenne Anne,
Boiteau JeanGuy,
Tomas Loic,
Hennequin Laurent,
Harris Craig S.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800304
Subject(s) - chemistry , hydroxylamine , cleave , hyaluronic acid , amide , carbamate , selectivity , small molecule , acetylation , molecule , organic chemistry , protecting group , cleavage (geology) , combinatorial chemistry , polymer chemistry , biochemistry , enzyme , genetics , geotechnical engineering , fracture (geology) , gene , engineering , biology , catalysis , alkyl
During our investigation to find suitable conditions to prepare very high molecular weight partially de‐acetylated hyaluronic acid (HA), we discovered a powerful new method to cleave amide bonds using hydroxylamine salts at neutral pH with remarkable selectivity over common carbamate protecting groups and other carbonyl functionality including unhindered esters.