Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

AG-E-79310 4-hydroxybutanal

Synonyms: AC1L3PHJ, AC1Q6QLF, CTK1A5850, AR-1G2812, A818440, ...

Enders, D. et al., Wang, M.Y. et al., Autrup, H. et al.

Enders, Vicario, Job, Wolberg, Müller,

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High impact information on EINECS 247-205-3

N-Nitrosopyrrolidine was oxidized by both rat and human esophagus in the alpha position, as measured by the formation of 2,4-dinitrophenylhydrazone derivative of 4-hydroxybutanal [1].
For the second intermediate 4 the asymmetric alpha-alkylation of an O-protected derivative of 4-hydroxybutanal was performed exploiting the SAMP/RAMP hydrazone alkylation methodology, and followed by a highly Z-selective Horner-Wadsworth-Emmons reaction under modified conditions [2].
The approximate values of Km and nu max for crotonaldehyde were 5.8 mM and 0.6 nmol/min/mg of protein and for 4-hydroxybutyraldehyde 14.1 mM and 1.7 nmol/min/mg of protein, for substrate concentrations between 1 and 8 mM, with microsomes from Aroclor pretreated rats [3].

References

Metabolism of N-nitrosamines by cultured human and rat esophagus. Autrup, H., Stoner, G.D. Cancer Res. (1982) [Pubmed]
Asymmetric total synthesis of (-)-callystatin A and (-)-20-epi-callystatin A employing chemical and biological methods. Enders, D., Vicario, J.L., Job, A., Wolberg, M., Müller, M. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
Identification of crotonaldehyde as a hepatic microsomal metabolite formed by alpha-hydroxylation of the carcinogen N-nitrosopyrrolidine. Wang, M.Y., Chung, F.L., Hecht, S.S. Chem. Res. Toxicol. (1988) [Pubmed]

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