100940-60-1Relevant articles and documents
The preparation of all-trans uniformly 13C-labeled retinal via a modular total organic synthetic strategy. Emerging central contribution of organic synthesis toward the structure and function study with atomic resolution in protein research
Creemers, Alain F. L.,Lugtenburg, Johan
, p. 6324 - 6334 (2002)
Uniformly [13C20]-labeled all-trans-retinal (1) has been prepared via a convergent modular total organic strategy with high isotope incorporation (>99%) and without isotope dilution starting from commercially available 99% enriched
A simple efficient synthesis of [23,24]-13C2-labeled bile salts as NMR probes of protein-ligand interactions
Tochtrop, Gregory P.,DeKoster, Gregory T.,Cistola, David P.,Covey, Douglas F.
, p. 433 - 435 (2002)
The synthesis of [23,24]-13C2-labeled bile salts is achieved through a steroidal side chain degradation and isotopic regeneration strategy. Three common bile acids were degraded to the corresponding C22 aldehyde by an oxidative decarboxylation followed by ozonolysis. The side chain was subsequently regenerated via a Horner-Emmons reaction using an ylide generated from 13C2-labeled bromoacetic acid. These compounds were used as probes of protein-bile salt interactions using two- and three-dimensional NMR techniques.
Syntheses of 13C2-labelled 11Z-retinals
McLean, Neville J.,Gansmuller, Axel,Concistre, Maria,Brown, Lynda J.,Levitt, Malcom H.,Brown, Richard C.D.
scheme or table, p. 8404 - 8410 (2011/11/12)
To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent 13C labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a 13C-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a 13C-containing ethoxy Bestmann-Ohira reagent. The 13C labels at C10 and C11 were introduced through the reaction of β-ionone with labelled triethyl phosphonoacetate.
