DOI: 10.1128/jb.137.1.129-136.1979. Characterization of mutationally altered dihydropteroate synthase and its ability to form a sulfonamide-containing dihydrofolate analog

Characterization of mutationally altered dihydropteroate synthase and its ability to form a sulfonamide-containing dihydrofolate analog

10.1128/jb.137.1.129-136.1979

Crossref journal-article

American Society for Microbiology

Journal of Bacteriology (235)

Abstract

Among spontaneous mutants of Escherichia coli selected for resistance against sulfonamides, thermosensitive strains were found. These were shown to possess a changed dihydropteroate synthase (EC 2.5.1.15), which had a substantially higher Km value for its normal substrate, p-aminobenzoic acid, and an about 150-fold higher Km for sulfonamides. The mutationally changed dihydropteroate synthase was found to be thermosensitive by in vitro assays. The thermosensitivity was used as an enzyme marker to demonstrate the complex formation between 2-amino-4-hydroxy-6-pyrophosphorylmethyl pteridine and sulfonamides by partially purified dihydropteroate synthase. The formation of folate from 2-amino-4-hydroxy-6-pyrophosphorylmethyl pteridine and p-aminobenzoylglutamic acid by dihydropteroate synthase was found to be very sensitive to inhibition by sulfonamides and very inefficient with the mutationally changed enzyme.

Bibliography

Swedberg, G., Castensson, S., & SkÃ¶ld, O. (1979). Characterization of mutationally altered dihydropteroate synthase and its ability to form a sulfonamide-containing dihydrofolate analog. Journal of Bacteriology, 137(1), 129â136.

Authors 3

G Swedberg (first)
S Castensson (additional)
O Sköld (additional)

References 16 Referenced 52

Barnett , E. B. , and I. G. Nixon . 1924 . The preparation of anilides and esters . Chem. News 129 : 190 - 191 . / Chem. News / The preparation of anilides and esters by Barnett E. B. (1924)
Blakley , R. L. 1960 . Crystalline dihydropteroylglutamic acid . Nature (London) 188 : 231 - 232 . (10.1038/188231a0) / Nature (London) / Crystalline dihydropteroylglutamic acid by Blakley R. L. (1960)
Bock , L , G. H. Miller , K. -J. Schaper , and J. K. Seydel . 1973 . Sulfonamide structure-activity relationships in a cell-free system. 2. Proof for the formation of a sulfonamide-containing folate analog . J. Med. Chem. 17 : 23 - 28 . (10.1021/jm00247a006) / J. Med. Chem. / Sulfonamide structure-activity relationships in a cell-free system. 2. Proof for the formation of a sulfonamide-containing folate analog by Bock L (1973)
Brown , G. M. 1962 . The biosynthesis of folic acid. II. Inhibition of sulfonamides . J. Biol. Chem. 237 : 536 - 540 . (10.1016/S0021-9258(18)93957-8) / J. Biol. Chem. / The biosynthesis of folic acid. II. Inhibition of sulfonamides by Brown G. M. (1962)
Edward , J. T. , H. S. Chang , and S. A. Samad . 1962 . Organic peroxides. IV. Catalysis of aroyl peroxide reactions by aluminium chloride: the direct introduction of o-aroyl groups into aromatic nuclei . Can. J. Chem. 40 : 804 - 810 . (10.1139/v62-118) / Can. J. Chem. / Organic peroxides. IV. Catalysis of aroyl peroxide reactions by aluminium chloride: the direct introduction of o-aroyl groups into aromatic nuclei by Edward J. T. (1962)
Kanaoka , Y. , K. Tanizawa , E. Sato , 0. Yonemitau , and Y. Ban . 1967 . Polyphosphate ester as a synthetic agent. IV. A novel preparation of aryl esters . Chem. Pharm. Bull. 15 ( 5 ): 593 - 595 . (10.1248/cpb.15.593) / Chem. Pharm. Bull. / Polyphosphate ester as a synthetic agent. IV. A novel preparation of aryl esters by Kanaoka Y. (1967)
Lowry , 0. H. , N. J. Rosebrough , A. L. Farr , and R. J. Randall . 1951 . Protein measurement with the Folin phenol reagent . J. Biol. Chem. 193 : 265 - 275 . (10.1016/S0021-9258(19)52451-6) / J. Biol. Chem. / Protein measurement with the Folin phenol reagent by Lowry 0. (1951)
Matsukawa , T. , S. Ban , and T. Imada . 1951 . Studies on chemotherapeutics. XX. Nitrobenzoic acid derivatives . J. Pharm. Soc. (Japan) 71 : 477 - 480 . (10.1248/yakushi1947.71.6_477) / J. Pharm. Soc. (Japan) / Studies on chemotherapeutics. XX. Nitrobenzoic acid derivatives by Matsukawa T. (1951)
Nowak , K. , and R. Krug . 1966 . Guanidine derivatives. I. Reactions between guanidine and p-nitrophenyl esters of several N-acylamino acids . Roczniki Chem. 40 : 931 - 934 . / Roczniki Chem. / Guanidine derivatives. I. Reactions between guanidine and p-nitrophenyl esters of several N-acylamino acids by Nowak K. (1966)
Pato , M. L. , and G. M. Brown . 1963 . Mechanisms of resistance of Escherichia coli to sulfonamides . Arch. Biochem. Biophys. 103 : 443 - 448 . (10.1016/0003-9861(63)90435-1) / Arch. Biochem. Biophys. / Mechanisms of resistance of Escherichia coli to sulfonamides by Pato M. L. (1963)
Richey , D. P. , and G. M. Brown . 1969 . The biosynthesis of folic acid. IX. Purification and properties of the enzymes required for the formation of dihydropteroic acid . J. Biol. Chem. 244 : 1582 - 1592 . / J. Biol. Chem. / The biosynthesis of folic acid. IX. Purification and properties of the enzymes required for the formation of dihydropteroic acid by Richey D. P. (1969)
Richey , D. P. , and G. M. Brown . 1970 . A comparison of the effectiveness with which p-aminobenzoic acid and p-aminobenzoylglutamic acid are used as substrate by dihydropteroate synthetase from Escherichia coli . Biochim. Biophys. Acta 222 : 237 - 239 . (10.1016/0304-4165(70)90376-4) / Biochim. Biophys. Acta / A comparison of the effectiveness with which p-aminobenzoic acid and p-aminobenzoylglutamic acid are used as substrate by dihydropteroate synthetase from Escherichia coli by Richey D. P. (1970)
Shiota , T. , C. M. Baugh , R. Jackson , and R. Dillard . 1969 . The enzymatic synthesis of hydroxymethyldihydropteridine pyrophosphate and dihydrofolate . Biochemistry 8 : 5022 - 5028 . (10.1021/bi00840a052) / Biochemistry / The enzymatic synthesis of hydroxymethyldihydropteridine pyrophosphate and dihydrofolate by Shiota T. (1969)
Shiota , T. , M. N. Diraely , and M. P. McCann . 1964 . The enzymatic synthesis of folate-like compounds from hydroxy-methyldihydropteridine pyrophosphate . J. Biol. Chem. 239 : 2259 - 2266 . (10.1016/S0021-9258(20)82229-7) / J. Biol. Chem. / The enzymatic synthesis of folate-like compounds from hydroxy-methyldihydropteridine pyrophosphate by Shiota T. (1964)
Skold , 0. 1976 . R factor-mediated resistance to sulfonamides by a plasmid-borne, drug-resistant dihydropteroate synthase . Antimicrob. Agents Chemother. 9 : 49 - 54 . (10.1128/AAC.9.1.49) / Antimicrob. Agents Chemother. / R factor-mediated resistance to sulfonamides by a plasmid-borne, drug-resistant dihydropteroate synthase by Skold 0. (1976)
Wiman , M. , G. Bertani , B. Kelly , and I. Sasaki . 1970 . Genetic map of Escherichia coli strain C . Mol. Gen. Genet. 107 : 1 - 31 . (10.1007/BF00433220) / Mol. Gen. Genet. / Genetic map of Escherichia coli strain C by Wiman M. (1970)

Dates

Type	When
Created	5 years, 7 months ago (Jan. 3, 2020, 11:01 a.m.)
Deposited	4 years, 1 month ago (July 29, 2021, 1:33 p.m.)
Indexed	1 year, 1 month ago (July 28, 2024, 7:16 a.m.)
Issued	46 years, 8 months ago (Jan. 1, 1979)
Published	46 years, 8 months ago (Jan. 1, 1979)
Published Print	46 years, 8 months ago (Jan. 1, 1979)

Funders 0

None

BibTeX

@article{Swedberg_1979, title={Characterization of mutationally altered dihydropteroate synthase and its ability to form a sulfonamide-containing dihydrofolate analog}, volume={137}, ISSN={1098-5530}, url={http://dx.doi.org/10.1128/jb.137.1.129-136.1979}, DOI={10.1128/jb.137.1.129-136.1979}, number={1}, journal={Journal of Bacteriology}, publisher={American Society for Microbiology}, author={Swedberg, G and Castensson, S and Sköld, O}, year={1979}, month=jan, pages={129–136} }

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