Organocatalysis with endogenous compounds: towards novel non-enzymatic reactions.

نویسندگان

  • David G Alberg
  • Thomas B Poulsen
  • Søren Bertelsen
  • Kasper L Christensen
  • Rune D Birkler
  • Mogens Johannsen
  • Karl Anker Jørgensen
چکیده

The aldol reaction of the endogeneous compounds acetone and methylglyoxal has been studied using organocatalysis in relation to biologically relevant non-enzymatic reactions. Under preparative conditions, 3-hydroxy-2,5-hexadione, known as Henze's ketol, is formed in high yield and with enantioselectivities up to 88% ee. Furthermore, Henze's ketol is also formed under simulated physiological conditions at micromolar scale, indicating that this reaction might take place in living organisms.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Asymmetric organocatalysis: from infancy to adolescence.

After an initial period of validating asymmetric organocatalysis by using a wide range of important model reactions that constitute the essential tools of organic synthesis, the time has now been reached when organocatalysis can be used to address specific issues and solve pending problems of stereochemical relevance. This Review deals with selected studies reported in 2006 and the first half o...

متن کامل

Palladium and organocatalysis: an excellent recipe for asymmetric synthesis.

The dual activation of simple substrates by the combination of organocatalysis and palladium catalysis has been successfully applied in a variety of different asymmetric transformations. Thus, the asymmetric a-allylation of carbonyl compounds, a-fluorination of acyl derivatives, decarboxylative protonation of β-dicarbonyl compounds, cyclization reactions of alkynyl carbonyl compounds and β-func...

متن کامل

Synthetic autocatalysts show organocatalysis of other reactions.

A molecule capable of both autocatalysis and organocatalysis was synthesized. The autocatalytic activity results from the self-complementary recognition sites provided by hydrogen bonding between heterocyclic subunits and the organocatalysis resides in an embedded thiourea function. The behavior of the molecule suggests both replication and metabolism can be engineered into synthetic compounds.

متن کامل

Cross-trienamines in Asymmetric Organocatalysis

Cross-conjugated trienamines are introduced as a new concept in asymmetric organocatalysis. These intermediates are applied in highly enantioselective Diels-Alder and addition reactions, providing functionalized bicyclo[2.2.2]octane compounds and γ'-addition products, respectively. The nature of the transformations and the intermediates involved are investigated by computational calculations an...

متن کامل

Aryl azo 5-arylidene-2,4-thiazolidinone dyes as novel antioxidant and antibacterial compounds

In the present study, nine bis-azo dyes based on 5-arylidene-2,4-thiazolidinone were obtained in two steps, using Knoevenagel condensation and azo coupling reactions. The structure of the dyes was confirmed on the basis of spectral data. Analysis of spectroscopic data shows that there is equilibrium between the azo and hydrazone tautomers for all dyes in solutions. Investigation of antioxidant ...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:
  • Bioorganic & medicinal chemistry letters

دوره 19 14  شماره 

صفحات  -

تاریخ انتشار 2009