The arsonomethyl analogue of 3-phosphoglycerate

Adams, S R; Sparkes, Michael J.; Dixon, H. B. F.

doi:10.1042/bj2130211

Cited by 26 publications

(19 citation statements)

References 17 publications

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“…DL-4-Arsono-2-benzylbutanoic acid was bound as well as its phosphorus analogue 2-benzyl-4-phosphonobutanoic acid, both of which were designed to resemble glycyl-L-phenylalanine (IC50 = 630pM; Cheung et al, 1980). Adams et al (1983) have described 4-arsono-2-hydroxybutanoic acid, the arsonomethyl analogue of 3-phosphoglycerate, which has a Km for phosphoglycerate kinase about 5-fold higher than that of 3-phosphoglycerate and a catalytic constant about 1300-fold smaller. The present work and this previous report provide the only examples of the interaction of arsonic acid substrate analogues and inhibitors with enzymes.…”

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confidence: 98%

Inhibitors of angiotensin-converting enzyme containing a tetrahedral arsenic atom

Galardy¹,

Kortylewicz²

1985

Biochemical Journal

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A series of tetrahedral oxo acids of Group VA and VIA elements and of silicon and boron were examined as inhibitors of angiotensin-converting enzyme. Arsenate is a competitive inhibitor with a Ki of 27 +/- 1 mM, at least 10-fold more potent than phosphate. Dimethylarsinate is a competitive inhibitor with a Ki of 70 +/- 9 mM, 2-fold more potent than dimethylphosphinate. Oxo acids of boron, silicon, antimony, sulphur and selenium are not inhibitors. On the basis of these results and the strong inhibition of this zinc metallopeptidase by substrate analogues containing a tetrahedral phosphorus atom, two substrate analogues containing a tetrahedral arsenic atom were prepared. 2-Arsonoacetyl-L-proline is a competitive inhibitor with a Ki of 18 +/- 7 mM, more than 2000-fold weaker than that of its phosphorus analogue 2-phosphonoacetyl-L-proline. 4-Arsono-2-benzylbutanoic acid is a mixed inhibitor with a Ki of 0.5 +/- 0.2 mM, indistinguishable in potency from its phosphorus analogue 2-benzyl-4-phosphonobutanoic acid.

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confidence: 98%

Inhibitors of angiotensin-converting enzyme containing a tetrahedral arsenic atom

Galardy¹,

Kortylewicz²

1985

Biochemical Journal

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“…The analogues of 3-phosphoglycerate used in the present study are isosteric with the natural substrate, and involve only the replacement of -O-PO3H2 either by -CH2-PO3H, or by -CH2-As03H,. These compounds have previously been shown to be substrates of phosphoglycerate kinase (Dixon & Sparkes, 1974;Orr & Knowles, 1974;Adams et al, 1983). The effect of 3-arsono-2-(arsonomethyl)propanoic acid, (H203As-CHR-),CH-CO,H, was also investigated, although this compound is not an isosteric analogue of the natural substrates and effectors of these enzymes; nevertheless parts of its molecule are isosteric with 2-phosphoglycerate and 2,3bisphosphoglycerate, and also with 2-phosphoglycollate, which is an inhibitor of yeast phosphoglycerate mutase, as reviewed by Rose (1980).…”

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confidence: 99%

The phosphonomethyl analogue of 3-phosphoglycerate is a potent competitive inhibitor of phosphoglycerate mutases

McALEESE¹,

Fothergill‐Gilmore²,

Dixon³

1985

Biochemical Journal

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The phosphonomethyl analogue of 3-phosphoglycerate (2-hydroxy-4-phosphonobutanoate) is a potent competitive inhibitor of cofactor-dependent phosphoglycerate mutase from yeast and of cofactor-independent phosphoglycerate mutase from wheat germ. For the yeast enzyme Ki is 1.3 mM (Km for substrate is 0.71 mM); for the wheatgerm enzyme Ki is 18 mM (Km for substrate is 0.86 mM). This analogue should be a useful tool for n.m.r. spectroscopic studies on the mechanism of action of the two mutases. The arsonomethyl analogue of 3-phosphoglycerate (4-arsono-2-hydroxybutanoate) was a relatively poor inhibitor.

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“…7,8 Esters of arsinic acids have been made in similar manner. 9,10 If an unsymmetrically substituted arsinic acid is dissolved in an † This paper is based on work presented at the 12th Symposium of the Japanese Arsenic Scientists' Society (JASS) held 5-6 November 2005 in Takizawa, Iwate Prefecture, Japan.…”

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confidence: 99%