Literature DB >> 14504283

CYP17 mutation E305G causes isolated 17,20-lyase deficiency by selectively altering substrate binding.

Daniel P Sherbet1, Dov Tiosano, Kerri M Kwist, Zeev Hochberg, Richard J Auchus.   

Abstract

Cytochrome p450c17 (CYP17) converts the C21 steroids pregnenolone and progesterone to the C19 androgen precursors dehydroepiandrosterone (DHEA) and androstenedione, respectively, via sequential 17alpha-hydroxylase and 17,20-lyase reactions. Disabling mutations in CYP17 cause combined 17alpha-hydroxylase/17,20-lyase deficiency, but rare missense mutations cause isolated loss of 17,20-lyase activity by disrupting interactions of redox partner proteins with CYP17. We studied an adolescent male with clinical and biochemical features of isolated 17,20-lyase deficiency, including micropenis, hypospadias, and gynecomastia, who is homozygous for CYP17 mutation E305G, which lies in the active site. When expressed in HEK-293 cells or Saccharomyces cerevisiae, mutation E305G retains 17alpha-hydroxylase activities, converting pregnenolone and progesterone to 17alpha-hydroxysteroids. However, mutation E305G lacks 17,20-lyase activity for the conversion of 17alpha-hydroxypregnenolone to DHEA, which is the dominant pathway to C19 steroids catalyzed by human CYP17 (the delta5-steroid pathway). In contrast, mutation E305G exhibits 11-fold greater catalytic efficiency (kcat/Km) for the cleavage of 17alpha-hydroxyprogesterone to androstenedione compared with wild-type CYP17. We conclude that mutation E305G selectively impairs 17,20-lyase activity for DHEA synthesis despite an increased capacity to form androstenedione. Mutation E305G provides genetic evidence that androstenedione formation from 17alpha-hydroxyprogesterone via the minor delta4-steroid pathway alone is not sufficient for complete formation of the male phenotype in humans.

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Year:  2003        PMID: 14504283     DOI: 10.1074/jbc.M307586200

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  38 in total

Review 1.  The syndrome of 17,20 lyase deficiency.

Authors:  Walter L Miller
Journal:  J Clin Endocrinol Metab       Date:  2011-11-09       Impact factor: 5.958

2.  Synthesis of halogenated pregnanes, mechanistic probes of steroid hydroxylases CYP17A1 and CYP21A2.

Authors:  Francis K Yoshimoto; Melissa C Desilets; Richard J Auchus
Journal:  J Steroid Biochem Mol Biol       Date:  2011-10-05       Impact factor: 4.292

Review 3.  Steroid 17-hydroxylase and 17,20-lyase deficiencies, genetic and pharmacologic.

Authors:  Richard J Auchus
Journal:  J Steroid Biochem Mol Biol       Date:  2016-02-06       Impact factor: 4.292

Review 4.  The next 150 years of congenital adrenal hyperplasia.

Authors:  Adina F Turcu; Richard J Auchus
Journal:  J Steroid Biochem Mol Biol       Date:  2015-06-03       Impact factor: 4.292

5.  Minor activities and transition state properties of the human steroid hydroxylases cytochromes P450c17 and P450c21, from reactions observed with deuterium-labeled substrates.

Authors:  Francis K Yoshimoto; Yishan Zhou; Hwei-Ming Peng; David Stidd; Jennifer A Yoshimoto; Kamalesh K Sharma; Susan Matthew; Richard J Auchus
Journal:  Biochemistry       Date:  2012-08-27       Impact factor: 3.162

Review 6.  Monogenic Disorders of Adrenal Steroidogenesis.

Authors:  Elizabeth S Baranowski; Wiebke Arlt; Jan Idkowiak
Journal:  Horm Res Paediatr       Date:  2018-06-06       Impact factor: 2.852

Review 7.  Human cytochrome P450 enzymes 5-51 as targets of drugs and natural and environmental compounds: mechanisms, induction, and inhibition - toxic effects and benefits.

Authors:  Slobodan P Rendic; F Peter Guengerich
Journal:  Drug Metab Rev       Date:  2018-08       Impact factor: 4.518

8.  A-ring modified steroidal azoles retaining similar potent and slowly reversible CYP17A1 inhibition as abiraterone.

Authors:  Mariana Garrido; Hwei-Ming Peng; Francis K Yoshimoto; Sunil K Upadhyay; Eugene Bratoeff; Richard J Auchus
Journal:  J Steroid Biochem Mol Biol       Date:  2014-02-06       Impact factor: 4.292

9.  Hypospadias and variants in genes related to sex hormone biosynthesis and metabolism.

Authors:  S L Carmichael; J S Witte; C Ma; E J Lammer; G M Shaw
Journal:  Andrology       Date:  2013-11-26       Impact factor: 3.842

Review 10.  The diverse chemistry of cytochrome P450 17A1 (P450c17, CYP17A1).

Authors:  Francis K Yoshimoto; Richard J Auchus
Journal:  J Steroid Biochem Mol Biol       Date:  2014-12-04       Impact factor: 4.292

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