Stereochemical dependence of the self-assembly of the immunoadjuvants Pam3Cys and Pam3Cys-Ser

Frank Reichel, Annie M. Roelofsen, Hubertus P.M. Geurts, Taina I. Hämäläinen, Martinus C. Feiters, Geert Jan Boons*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The lipopeptide tripalmitoyl-S-glycerylcysteine (Pam3Cys) is derived from the N-terminal part of bacterial lipopeptides and is a polyclonal B- lymphocyte and macrophage activator. Derivatives of Pam3Cys constitute highly potent, nontoxic immunoadjuvants, and lipopeptide-antigen conjugates have found important applications as novel fully synthetic low-molecular- weight vaccines. To establish a possible correlation between molecular structure, aggregation properties, and biological activities, we have studied the self-assembly and monolayer properties of a range of Pam3Cys derivatives using transmission electron microscopy (TEM) and a Langmuir-film balance combined with a Brewster angle microscopy (BAM). It was found that the chirality of the glyceryl moiety and the additional serine unit impacted on the mode of aggregation and the monolayer properties. Correlations are discussed between these physicochemical properties and biological activities.

Original languageEnglish
Pages (from-to)7989-7997
Number of pages9
JournalJournal of the American Chemical Society
Volume121
Issue number35
DOIs
Publication statusPublished - 8 Sept 1999
Externally publishedYes

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