caffeine degradation III (bacteria, via demethylation)

Summers RM, Seffernick JL, Quandt EM, Yu CL, Barrick JE, Subramanian MV. Caffeine Junkie: an Unprecedented Glutathione S-Transferase-Dependent Oxygenase Required for Caffeine Degradation by Pseudomonas putida CBB5. Journal of Bacteriology. 2013 Jun 28;195(17):3933–9. doi: 10.1128/jb.00585-13.; Summers RM, Louie TM, Yu C, Gakhar L, Louie KC, Subramanian M. Novel, Highly Specific N -Demethylases Enable Bacteria To Live on Caffeine and Related Purine Alkaloids. J Bacteriol. 2012 Apr 15;194(8):2041–9. doi: 10.1128/jb.06637-11.; Summers RM, Louie TM, Yu CL, Subramanian M. Characterization of a broad-specificity non-haem iron N-demethylase from Pseudomonas putida CBB5 capable of utilizing several purine alkaloids as sole carbon and nitrogen source. Microbiology (Reading). 2011 Feb;157(Pt 2):583–92. doi: 10.1099/mic.0.043612-0. PMID: 20966097.; Yu CL, Louie TM, Summers R, Kale Y, Gopishetty S, Subramanian M. Two Distinct Pathways for Metabolism of Theophylline and Caffeine Are Coexpressed in Pseudomonas putida CBB5. J Bacteriol. 2009 Jul 15;191(14):4624–32. doi: 10.1128/jb.00409-09.; Dash SS, Gummadi SN. Catabolic pathways and biotechnological applications of microbial caffeine degradation. Biotechnol Lett. 2006 Dec;28(24):1993–2002. doi: 10.1007/s10529-006-9196-2. PMID: 17009088.; Mazzafera P. Catabolism of caffeine in plants and microorganisms. Front Biosci. 2004 May 01;9():1348–59. doi: 10.2741/1339. PMID: 14977550.; HOHNLOSER W, OSSWALD B, LINGENS F. Enzymological Aspects of Caffeine Demethylation and Formaldehyde Oxidation byPseudomonas putidaC1. Hoppe-Seyler´s Zeitschrift für physiologische Chemie. 1980 Jan;361(2):1763–6. doi: 10.1515/bchm2.1980.361.2.1763.; Woolfolk CA. Metabolism of N-methylpurines by a Pseudomonas putida strain isolated by enrichment on caffeine as the sole source of carbon and nitrogen. J Bacteriol. 1975 Sep;123(3):1088–106. doi: 10.1128/jb.123.3.1088-1106.1975.

Metabolites

1,7-Dimethylxanthine

Formula: C7H8N4O2 (180.0647228)

CAS ID: 611-59-6

7-Methylxanthine

Formula: C6H6N4O2 (166.0490736)

CAS ID: 552-62-5

Caffeine

Formula: C8H10N4O2 (194.080372)

CAS ID: 58-08-2

Calcium cation

Formula: Ca (39.962591)

CAS ID: 14127-61-8

Cobalt ion

Formula: Co (58.933198)

CAS ID: 22541-53-3

Copper

Formula: Cu (62.929599)

CAS ID: 7440-50-8

Fe2+

Formula: Fe (55.934939)

CAS ID: 15438-31-0

Formaldehyde

Formula: CH2O (30.0105642)

CAS ID: 50-00-0

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Hydrogen peroxide

Formula: H2O2 (34.0054792)

CAS ID: 7722-84-1

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Mercury(2+)

Formula: Hg (201.970632)

CAS ID: 14302-87-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Silver

Formula: Ag (106.905095)

CAS ID: 7440-22-4

Theobromine

Formula: C7H8N4O2 (180.0647228)

CAS ID: 83-67-0

Xanthine

Formula: C5H4N4O2 (152.0334244)

CAS ID: 69-89-6

Zinc cation

Formula: Zn (63.929145)

CAS ID: 23713-49-7

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9



Enzyme

EC Number name full name note
1.-.-.-
1.14.13.178 methylxanthine N1-demethylase caffeine:oxygen oxidoreductase (N1-demethylating)
1.14.13.179 methylxanthine N3-demethylase theobromine:oxygen oxidoreductase (N3-demethylating)


Proteins

Protein ID name full name
H9N289 ndmA Methylxanthine N1-demethylase NdmA
H9N290 ndmB Methylxanthine N3-demethylase NdmB
H9N291 ndmD Oxidoreductase NdmD