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Cited by 313

The DOI matches its Crossref record; 21 of the 21 references it cites were found in a registry or an index.

Covalent Attachment and Derivatization of Poly(l-lysine) Monolayers on Gold Surfaces As Characterized by Polarization−Modulation FT-IR Spectroscopy

Frey, Brian L., Corn, Robert M.·1996·Analytical Chemistry
DOI 10.1021/ac9605861
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Abstract

A monolayer of poly( l -lysine) (PL) is attached covalently via amide bonds to an alkanethiol self-assembled monolayer (SAM) on a gold surface. The amide bond is formed in two steps: the terminal carboxylic acid groups of an 11-mercaptoundecanoic acid (MUA) SAM are first activated to the N -hydroxysulfosuccinimide (NHSS) ester, followed by reaction of this MUA-NHSS ester monolayer with the amino groups of PL to create multiple amide bond linkages to the surface. The reactivity and packing density of the MUA-NHSS esters are investigated in detail by reacting these intermediates with ammonia (NH 3 ). In the NH 3 experiments, approximately 50% of the carboxylic acids in the MUA monolayer are converted to amides during the first cycle of this two-step surface reaction. This reaction yield of 50% is limited by the steric packing of the NHSS ester intermediate. However, after three cycles of MUA activation to the NHSS ester and reaction with NH 3, nearly all of the MUA molecules (∼80%) are converted to amides. Polarization−modulation Fourier transform infrared reflection−absorption spectroscopy (PM-FT-IRRAS) is employed to study both the NH 3 and PL reactions on the gold surface. The PM-FT-IRRAS spectrum of a covalently attached PL monolayer indicates that amide bonds are formed with the underlying MUA molecules. This conclusion is confirmed by the fact that the covalent PL monolayer resists desorption despite immersion into solutions of pH < 2 or pH > 12. Finally, the PL is derivatized with a bifunctional NHSS ester−maleimide molecule either by reaction in solution prior to covalent attachment or by reaction with PL already adsorbed to the surface. Up to 50% of the total number of lysine amino groups are converted to maleimide groups, which can be used for the subsequent attachment of sulfhydryl-containing biomolecules.

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Metadata

Authors
Frey, B. L., & Corn, R. M.
Venue
Analytical Chemistry
Publisher
American Chemical Society (ACS)
Published
1996-01-01
Volume
68
Issue
18
Pages
3187-3193
ISSN
  • 0003-2700 (ISSN-L)
  • 1520-6882
DOI
10.1021/ac9605861
OpenAlex
W2158175581
Cited by
313
References
21
FWCI
2.97
Type
journal article
Language
en
Open access
closed

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