Flexible Method for Conjugation of Phenolic Lignin Model Compounds to Carrier Proteins

Gao, Ruili; Lu, Fachuang; Zhu, Yimin; Hahn, Michael G.; Ralph, John

doi:10.1021/acs.jafc.6b04273

Title: Flexible Method for Conjugation of Phenolic Lignin Model Compounds to Carrier Proteins

Journal Article · Tue Oct 11 00:00:00 EDT 2016 · Journal of Agricultural and Food Chemistry

DOI:https://doi.org/10.1021/acs.jafc.6b04273· OSTI ID:1328600

Gao, Ruili ^[1]; Lu, Fachuang ^[1]; Zhu, Yimin ^[2]; Hahn, Michael G. ^[3]; Ralph, John ^[1]

Department of Biochemistry, University of Wisconsin—Madison, Madison, Wisconsin 53706, United States, DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin—Madison, Madison, Wisconsin 53726, United States
Department of Chemistry, The Pennsylvania State University, Altoona College, 3000 Ivyside Park, Altoona, Pennsylvania 16601, United States
Complex Carbohydrate Research Center, The University of Georgia, Athens, Georgia 30602, United States

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 ¹⁵N- and ¹³C-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. As a result, this loading is suitable for attempting to raise new antibodies to plant lignins and for screening.

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Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: SC0006930

OSTI ID:: 1328600

Alternate ID(s):: OSTI ID: 1331814

Journal Information:: Journal of Agricultural and Food Chemistry, Journal Name: Journal of Agricultural and Food Chemistry Vol. 64 Journal Issue: 41; ISSN 0021-8561

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 3 works

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Title: Flexible Method for Conjugation of Phenolic Lignin Model Compounds to Carrier Proteins

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