40856-55-1

Upstream product

• 41088-87-3 N-benzoyl-L-homoserine 
• 67-56-1 methanol 
• 113304-18-0 N-benzoyl-2(S)-tert-butyl-4-methylene-1,3-oxazolidin-5-one 
• 6305-38-0 (S)-(-)-α-amino-γ-butyrolactone hydrobromide 
• 98-88-4 benzoyl chloride 
• 2185-03-7 L-homoserine lactone hydrochloride 

Downstream Products

• 296766-73-9 (1S)-N-[3-hydroxy-1-(hydroxymethyl)propyl]benzamide 

Relevant academic research and scientific papers

Diastereoselective addition of α-hydroxyalkyl and α-alkoxyalkyl radicals to chiral 4-methyleneoxazolidin-5-ones

A method for preparing optically active homoserine derivatives via the photoinduced radical additions of alcohols and ethers to the chiral 4- methyleneoxazolidin-5-ones 1 and 2 has been achieved. These photoadducts, however, are readily prone to epimerization under the conditions required for their deprotection.

N → π? Interactions in N-Acyl Homoserine Lactone Derivatives and Their Effects on Hydrolysis Rates

N-Acyl homoserine lactones (AHLs) mediate population-wide behavioral changes in Gram-negative bacteria through quorum sensing (QS), a process shown to regulate virulence, biofilm formation, and other phenotypes that impact human health. AHLs have been proposed to contain an n → π? interaction that reduces the molecules' susceptibility to signal inactivation via lactone hydrolysis. In this work, seven AHL derivatives were modeled via gas-phase DFT calculations, implicit solvent DFT calculations, and MD simulations. Each derivative was then synthesized and hydrolyzed to probe the relationship between the strength of the orbital interaction and hydrolysis rate. The data obtained support that an increase in n → π? energy (En→π?) correlates to a decrease in the hydrolysis rate constant (kobs). Further, the observed variation in these rates demonstrates that AHL hydrolysis can be modified by manipulating steric and electronic effects that alter the electrophilicity of the lactone carbonyl. These results help to elucidate nature's choice of AHLs as agents of density-dependent bacterial communication and could inform the design of AHL-based quorum sensing modulators.

Expeditious novel routes to enantiopure 3-amino tetrahydrofuran hydrochloride

The synthesis of chemically and enantiomerically pure (S)-3-amino tetrahydrofuran hydrochloride starting from the natural amino acids, l-aspartic acid or l-methionine is described. The process involves no chromatography and can be easily carried out on a large scale. The enantiopurity of the final product was established by NMR and chiral HPLC methods.

MODULATION OF BACTERIAL QUORUM SENSING WITH SYNTHETIC LIGANDS

The present invention provides compounds and methods for modulation of the quorum sensing of bacteria. In an embodiment, the compounds of the present invention are able to act as replacements for naturally occurring bacterial quorum sensing ligands in a l

Studies toward the synthesis of (+)-palustrine: The first asymmetric synthesis of (-)-methyl palustramate

The stereoselective synthesis of (-)-methyl palustramate, a possible intermediate for the synthesis of (+)-palustrine, is described. The key step of the synthesis is a conformationally restricted Claisen rearrangement to afford the highly functionalized 1-benzylpipecolic ester 10. In addition, a new procedure for debenzylation of 1-benzylpiperidines (Li, NH2CH2)2, Et3N, THF) was used to remove the benzyl protecting group where traditional methods failed.