Merck
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  • Immunomodulation and the quorum sensing molecule 3-oxo-C12-homoserine lactone: the importance of chemical scaffolding for probe development.

Immunomodulation and the quorum sensing molecule 3-oxo-C12-homoserine lactone: the importance of chemical scaffolding for probe development.

Chemical communications (Cambridge, England) (2013-01-19)
Amanda L Garner, Jing Yu, Anjali K Struss, Gunnar F Kaufmann, Vladimir V Kravchenko, Kim D Janda
ABSTRACT

As a guide for chemical probe design, focused analogue synthetic studies were undertaken upon the lactone ring of 3-oxo-C(12)-homoserine lactone. We have concluded that hydrolytic instability of the heterocyclic ring is pivotal for its ability to modulate immune signaling and probe preparation was aligned with these findings.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(S)-α-Amino-γ-butyrolactone hydrochloride, 97%
Sigma-Aldrich
α-Amino-γ-butyrolactone hydrobromide, 99%
Sigma-Aldrich
L-Homoserine lactone hydrochloride
Sigma-Aldrich
L-Homoserine
Sigma-Aldrich
Dihydro-3-amino-2-(3H)-furanone, AldrichCPR
Sigma-Aldrich
γ-Butyrolactone, ReagentPlus®, ≥99%
Sigma-Aldrich
4-Hydroxybutanoic acid lactone, ≥98%, FCC, FG