PMID: 708699Oct 3, 1978Paper

Affinity labeling of histamine N-methyltransferase by 2',3'-dialdehyde derivatives of S-adenosylhomocysteine and S-adenosylmethionine. Kinetics of inactivation

Biochemistry
R T BorchardtB S Wu

Abstract

S-Adenosyl-L-methionine (AdoMet), S-adenosyl-L-homocysteine (L-AdoHcy), and related ribonucleosides have been oxidized with periodic acid to the corresponding 2',3'-dialdehydes. Both AdoMet dialdehyde and L-AdoHcy dialdehyde were observed to rapidly and irreversibly inactivate histamine N-methyltransferase (HMT). Equally active as an irreversible inhibitor was S-adenosyl-D-homocysteine dialdehyde (D-AdoHcy dialdehyde), which is consistent with the known affinity of HMT for S-adenosyl-D-homocysteine (D-AdoHcy). Other analogues of AdoHcy dialdehyde (S-adenosyl-L-cysteine dialdehyde, S-adenosyl-L-homocysteine sulfoxide dialdehyde, and adenosine dialdehyde) also produced irreversible inactivation of HMT, but at predictably slower rates. The corresponding acyclic 2',3'-ribonucleosides, which were obtained by NaBH4 reduction of the ribonucleosides dialdehydes, were found to be very weak, reversible inhibitors of HMT. Kinetic analysis of the inactivation of HMT produced by L-AdoHcy dialdehyde, AdoMet dialdehyde, and D-AdoHcy dialdehyde suggested mechanisms involving the formation of dissociable enzyme-inhibitor complexes prior to irreversible inactivation. Studies using L-[2,8-3H] AdoHcy dialdehyde revealed that incorporation of radio...Continue Reading

References

Oct 10, 1977·Biochemical and Biophysical Research Communications·R T BorchardtB S Wu
Feb 6, 1976·The Journal of Organic Chemistry·R T BorchardtY S Wu
Dec 28, 1966·Biochimica Et Biophysica Acta·T W Kwon, H S Olcott
Feb 12, 1962·Biochimica Et Biophysica Acta·Z A SHABAROVAJ BADDILEY

Citations

Apr 23, 2003·European Journal of Pharmacology·P Nickolas ShepelJonathan D Geiger
Oct 11, 2015·Journal of Pharmaceutical Sciences·Katharine Barbara SchowenMichael S Wolfe
Nov 1, 1986·Analytical Biochemistry·P H Stern, R M Hoffman
Apr 16, 1984·Biochemical and Biophysical Research Communications·B T Keller, R T Borchardt

Related Concepts

Affinity Labels
Histamine N-Methyltransferase
Homocysteine
Methyltransferase
In Vivo NMR Spectroscopy
S-Adenosylhomocysteine
Gumbaral
Infrared Spectrophotometry
Structure-Activity Relationship

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