285-52-9Relevant articles and documents
Efficient and stereospecific synthesis of (z)-Hex-3-enedioic acid, a key intermediate for Gly-Gly cis olefin isostere
Perlman,Albeck
, p. 4443 - 4449 (2000)
(z)-Hex-3-enedioic acid, a key intermediate in the synthesis of (z)-5-amino-3-pentenoic acid (a Gly-Gly cis olefin isostere), was synthesized by a short and efficient procedure of sequential oxidations. Thus, selective mono epoxidation of 1,4-cyclohexadiene was followed by periodate oxidation to the appropriate dialdehyde. Finally, Jones oxidation of the dialdehyde afforded the corresponding diacid product.
Chemical and bacterial reduction of azo-probes: Monitoring a conformational change using fluorescence spectroscopy
Rattray, Nicholas J.W.,Zalloum, Waleed A.,Mansell, David,Latimer, Joe,Jaffar, Mohammed,Bichenkova, Elena V.,Freeman, Sally
, p. 2758 - 2766 (2013/04/10)
Sterically constrained probes 2,4-O-bisdansyl-6,7-diazabicyclo[3.2.1]oct-6- ene (8) and 2,4-O-bispyrenoyl-6,7-diazabicyclo[3.2.1]oct-6-ene (9) exhibit specific dimer fluorescent characteristics (λmax 555 nm and 511 nm, respectively), attributed to the 2,4-diaxial arrangement of the dansyl or pyrene groups. Reduction of the azo-conformational locking group in (8) and (9) yielded 1,3-bisdansyl-4,6-diaminocyclohexane (16) and 1,3-bispyrenoyl-4,6- diaminocyclohexane (17) in the tetra-equatorial chair conformation, thus minimising interaction of the bisdansyl or bispyrenoyl groups. This induces a change in fluorescence from a cooperative green emission dimer band to a blue-shifted, monomer type fluorescence, with λmax 448 nm and 396 nm for the reduced forms (16) and (17), respectively. The azo-bond conformational lock can either be reduced under biomimetic conditions (using sodium dithionite) or with bacteria (Clostridium perfringens or Escherichia coli) utilising azo-reductase enzymes. These fluorescent probes have the potential to specifically detect azo-reductase expressing bacteria.
Fluorescent probe for detection of bacteria: Conformational trigger upon bacterial reduction of an azo bridge
Rattray, Nicholas J. W.,Zalloum, Waleed A.,Mansell, David,Latimer, Joe,Schwalbe, Carl H.,Blake, Alexander J.,Bichenkova, Elena V.,Freeman, Sally
scheme or table, p. 6393 - 6395 (2012/07/17)
Using biomimetic chemical reduction or Clostridium perfringens cell extract containing azoreductase, the dimer-fluorescent probe 2,4-O-bisdansyl-6,7- diazabicyclooct-6-ene, which possesses a conformationally constrained cis-azo bridge, is reduced to the t
