Guanidinium receptors

M -Dialkyldiazacrown ethers and their precursors fcis(alkylamino) derivatives of tri- and tetraethylene glycols were prepared <96CCCC622>. New hydroxy-bearing dibenzo-azocrown ethers have been conveniently prepared utilizing l,3-Ws(2-formylphenoxy)-2-propanol and a diamine, followed by reduction of the intermediate diimine <96P1197>. Fluorescent photoinduced electron transfer sensor 5 with monoaza-18-crown-6 and guanidinium receptor units demonstrated a fluorescence with T -aminobutyric acid in a mixed... 

Houk RJT, Tobey SL, Anslyn EV (2005) Abiotic Guanidinium Receptors for Anion Molecular Recognition and Sensing. 255 199-229 Hue I, see Brizard A (2005) 256 167-218... 

Houk RJT, Tobey SL, Anslyn EV (2005) Abiotic Guanidinium Receptors for Anion Molecular... 

Chiral bicyclic guanidinium receptors (e.g. 12-14, S,S-configuration shown) have been developed in our group from aminoacid precursors [16]. Improved synthetic procedures for such compounds were later reported by Schmidtchen [17] (who in 1980 presented a first type of achiral bicycloguanidinium hosts [18] that form complexes with several oxoanions [19]). Most derivatives are highly... 

Bicyclic guanidinium derivatives have also been incorporated into bis(guanidinium) receptors capable of recognising tetrahedral oxoanions, particularly polyphosphate residues of important biological molecules. The flexibility of receptor 4.31 allows the two guanidinium arms to swing into a mutually perpendicular arrangement in order to effectively complex polyphosphates even in water. 

Metzger, A., Peschke, W., Schmidtchen, F. P, A Convenient access to chiral monofunctionalized bicyclic guanidinium receptor groups. Synthesis-Stuttgart 1995, 566-570. 

Houk RJT, Tobey SL, Anslyn EV (2005) Abiotic Guanidinium Receptors for Anion Molecular Recognition and Sensing. 255 199-229 IshiiA, Nakayama J (2005) Carbodithioic Acid Esters. 251 181-225 Ishii A, Nakayama J (2005) Carboselenothioic and Carbodiselenoic Acid Derivatives and Related Compounds. 251 227-246 Jones W, see Trask AV (2005) 254 41-70 Kambe N, see Fujiwara S-i (2005) 251 87-140... 

These acyl guanidinium receptors combine several advantages compared with simple guanidines this makes them attractive candidates for the binding of car-boxylates ... 

The C,MO-macrocycles continue to be of synthetic interest, in that the A -appendage can be so readily modified e.g., guanidinium receptors <03JA8270> and lariat ethers <03CC2536>, as well as there is diminished strain relative to C-bonded counter-parts. Spironaphthoxazines... 

Another interesting development is the use of bicyclic guanidinium receptors as heteroditopic systems for the enantioselective recognition of amino acids. In this case the guanidinium fragment was combined via a flexible linker with a crown ether moiety in order to promote the simultaneous binding of the carboxylate anion and the ammonium cation belonging to a zwitterionic amino acid [45]. 

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