200273-93-4

Upstream product

• 52577-04-5 p-xylylene-α,α'-bis(phosphonic acid dimethyl ester) 

Downstream Products

• 375792-85-1 p-xylylene-α,α'-bis(phosphonic acid mono-3-[3'-nitro-4'-(tert-butyloxycarboxyamino-methyl)phenylmethyl]phenyl monomethyl ester) 

Relevant academic research and scientific papers

Towards synthetic adrenaline receptors - Shape-selective adrenaline recognition in water

In spite of their key role in signal transduction, the mechanism of action of adrenergic receptors is still poorly understood. We have imitated the postulated binding pattern of the large membrane protein with a small, rationally designed synthetic host molecule. Experimental evidence is presented for the simultaneous operation of electrostatic attraction, hydrogen bonds, π stacking, and hydrophobic interactions. By virtue of this combination of weak attractive forces, adrenaline derivatives in water are bound with high shape selectivity for the slim dopamine skeleton. We think that these findings support the postulated cooperative interplay of noncovalent interactions in the natural receptors. In addition, they provide access to a new type of adrenaline sensor. This may be the first step towards an artificial signal-transduction system.

Toward synthetic adrenaline receptors: Strong, selective, and biomimetic recognition of biologically active amino alcohols by bisphosphonate receptor molecules

Xylylene bisphosphonates represent a new class of artificial receptor molecules for alkylammonium ions (Schrader, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2649-2651). Molecular recognition takes place in a 1:1 chelate- binding mode, and an almost ideal array of short, linear hydrogen bonds is created that guarantees maximum electrostatic and hydrogen-bond interactions. The host molecule, which was designed to imitate the natural adrenergic receptor, is selective for 1,2- and 1,3-amino alcohols due to formation of an additional cooperative hydrogen bond between the phosphonate anion and the hydroxyl groups. Biologically important amino alcohols such as glucosamine, 1-aminosorbitol, ephedrine, and the β-blocker propranolol are bound in DMSO with K(a) values between 60 000 and 130 000 M-1. Secondary amines are complexed at least as strongly as their primary counterparts. The phosphonate ester groups allow lateral recognition of the substate. This could be demonstrated for adrenaline model compounds that were recognized by phosphonates carrying extended aromatic ester groups for Π,Π-interactions.