Open AccessFlexible Method for Conjugation of Phenolic Lignin Model Compounds to Carrier Proteins
Author(s) -
Ruili Gao,
Fachuang Lu,
Yimin Zhu,
Michael G. Hahn,
John Ralph
Publication year - 2016
Publication title -
journal of agricultural and food chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.203
H-Index - 297
eISSN - 1520-5118
pISSN - 0021-8561
DOI - 10.1021/acs.jafc.6b04273
Subject(s) - chemistry , lignin , bovine serum albumin , amine gas treating , cationic polymerization , hapten , ether , conjugated system , lysine , organic chemistry , bioconjugation , yield (engineering) , dimer , ethylenediamine , combinatorial chemistry , amino acid , biochemistry , antibody , polymer , materials science , metallurgy , immunology , biology
Linking lignin model compounds to carrier proteins is required either to raise antibodies to them or to structurally screen antibodies raised against lignins or models. This paper describes a flexible method to link phenolic compounds of interest to cationic bovine serum albumin (cBSA) without interfering with their important structural features. With the guaiacylglycerol-β-guaiacyl ether dimer, for example, the linking was accomplished in 89% yield with the number of dimers per carrier protein being as high as 50; NMR experiments on a 15 N- and 13 C-labeled conjugation product indicated that 13 dimers were added to the native lysine residues and the remainder (∼37) to the amine moieties on the ethylenediamine linkers added to BSA; ∼32% of the available primary amine groups on cBSA were therefore conjugated to the hapten. This loading is suitable for attempting to raise new antibodies to plant lignins and for screening.