The Enzyme Database

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EC 2.5.1.153     
Accepted name: adenosine tuberculosinyltransferase
Reaction: tuberculosinyl diphosphate + adenosine = 1-tuberculosinyladenosine + diphosphate
Glossary: tuberculosinyl diphosphate = halima-5,13-dien-15-yl diphosphate
Other name(s): Rv3378c (locus name)
Systematic name: tuberculosinyl-diphosphate:adenosine tuberculosinyltransferase
Comments: The enzyme, characterized from the bacterial pathogen Mycobacterium tuberculosis, produces 1-tuberculosinyladenosine, an unusual terpene nucleoside that acts as a phagolysosome disruptor by neutralizing the pH, resulting in swelling of the lysosome and obliteration of its multilamellar structure.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Layre, E., Lee, H.J., Young, D.C., Martinot, A.J., Buter, J., Minnaard, A.J., Annand, J.W., Fortune, S.M., Snider, B.B., Matsunaga, I., Rubin, E.J., Alber, T. and Moody, D.B. Molecular profiling of Mycobacterium tuberculosis identifies tuberculosinyl nucleoside products of the virulence-associated enzyme Rv3378c. Proc. Natl. Acad. Sci. USA 111 (2014) 2978–2983. [DOI] [PMID: 24516143]
2.  Young, D.C., Layre, E., Pan, S.J., Tapley, A., Adamson, J., Seshadri, C., Wu, Z., Buter, J., Minnaard, A.J., Coscolla, M., Gagneux, S., Copin, R., Ernst, J.D., Bishai, W.R., Snider, B.B. and Moody, D.B. In vivo biosynthesis of terpene nucleosides provides unique chemical markers of Mycobacterium tuberculosis infection. Chem. Biol. 22 (2015) 516–526. [DOI] [PMID: 25910243]
3.  Buter, J., Cheng, T.Y., Ghanem, M., Grootemaat, A.E., Raman, S., Feng, X., Plantijn, A.R., Ennis, T., Wang, J., Cotton, R.N., Layre, E., Ramnarine, A.K., Mayfield, J.A., Young, D.C., Jezek Martinot, A., Siddiqi, N., Wakabayashi, S., Botella, H., Calderon, R., Murray, M., Ehrt, S., Snider, B.B., Reed, M.B., Oldfield, E., Tan, S., Rubin, E.J., Behr, M.A., van der Wel, N.N., Minnaard, A.J. and Moody, D.B. Mycobacterium tuberculosis releases an antacid that remodels phagosomes. Nat. Chem. Biol. 15 (2019) 889–899. [DOI] [PMID: 31427817]
[EC 2.5.1.153 created 2011 as EC 3.1.7.8 and EC 3.1.7.9, transferred 2020 to EC 2.5.1.153]
 
 
EC 3.1.7.8      
Transferred entry: tuberculosinol synthase. Now known to be partial activity of EC 2.5.1.153, adenosine tuberculosinyltransferase.
[EC 3.1.7.8 created 2011, deleted 2020]
 
 
EC 3.1.7.9      
Transferred entry: isotuberculosinol synthase. Now known to be partial activity of EC 2.5.1.153, adenosine tuberculosinyltransferase.
[EC 3.1.7.9 created 2011, deleted 2020]
 
 
EC 5.5.1.16     
Accepted name: halimadienyl-diphosphate synthase
Reaction: geranylgeranyl diphosphate = tuberculosinyl diphosphate
For diagram of diterpenoid biosynthesis, click here
Glossary: tuberculosinyl diphosphate = halima-5,13-dien-15-yl diphosphate
Other name(s): Rv3377c; halimadienyl diphosphate synthase; tuberculosinol diphosphate synthase; halima-5(6),13-dien-15-yl-diphosphate lyase (cyclizing); halima-5,13-dien-15-yl-diphosphate lyase (decyclizing)
Systematic name: halima-5,13-dien-15-yl-diphosphate lyase (ring-opening)
Comments: Requires Mg2+ for activity. This enzyme is found in pathogenic prokaryotes such as Mycobacterium tuberculosis but not in non-pathogens such as Mycobacterium smegmatis so may play a role in pathogenicity. The product of the reaction is subsequently dephosphorylated yielding tuberculosinol (halima-5,13-dien-15-ol).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Nakano, C., Okamura, T., Sato, T., Dairi, T. and Hoshino, T. Mycobacterium tuberculosis H37Rv3377c encodes the diterpene cyclase for producing the halimane skeleton. Chem. Commun. (Camb.) (2005) 1016–1018. [DOI] [PMID: 15719101]
[EC 5.5.1.16 created 2008, modified 2012]
 
 


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