Ligands Chemistry



One of our recurrent works is the development and/or the synthesis of some derivatives involved in affinity mechanism with certain proteins. Those derivatives are called ligands and may act following the case, as a protein inhibitor or a protein activator. Two interesting examples are given here concerning the synthesis of tridecylstigmateline (TDS) (see fig. 1) and 4-hydroxynonylquinoleyl-N-oxyde (NQNO) (see fig. 2) which are two cytochrome b6f inhibitors commonly used in order to chock the cytochrome structure prior crystallization (see Stroebel, 2003 and Baymann, 2006 as example of application).

Scheme 1: synthetic pathway for TDS according to Höfle et al. (Höfle, 1984)



Scheme 2: synthetic pathway for NQNO according to Wells (Wells, 1952).

References

F. Baymann, F. Giusti, D. Picot, and W. Nitschke, The ci/bH moiety in the b6f complex studied by EPR: A pair of strongly interacting hemes, Proc. Nat. Acad. Sci. USA, 104, 519-524, 2007.

G. Höfle, B. Kunze, C. Zorzin, H. Reichenbach, Antibiotika aus Gleitenden bakterien, XXIII. Stigmatellin A und B-zwei neue Antibiotika aus Stigmatella aurantiaca (Myxobacterales), Liebigs Ann. Chem., 12, 1883-1904, 1984.

D. Stroebel, Y. Choquet, J-L. Popot and Daniel Picot, An atypical haem in the cytochrome b6f complex, Nature, 426, 413-418, 2003.

I. C. Wells, ANTIBIOTIC SUBSTANCES PRODUCED BY PSEUDOMONAS AERUGINOSA. SYNTHESES OF PYO Ib, PYO Ic, AND PYO III , J. Biol. Chem., 196, 331-340, 1952. And references therein.

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