superpathway of CMP-sialic acids biosynthesis

Gurung MK, Ræder IL, Altermark B, Smalås AO. Characterization of the sialic acid synthase from Aliivibrio salmonicida suggests a novel pathway for bacterial synthesis of 7-O-acetylated sialic acids. Glycobiology. 2013 Jul;23(7):806–19. doi: 10.1093/glycob/cwt018. PMID: 23481098.; Murkin AS, Chou WK, Wakarchuk WW, Tanner ME. Identification and mechanism of a bacterial hydrolyzing UDP-N-acetylglucosamine 2-epimerase. Biochemistry. 2004 Nov 09;43(44):14290–8. doi: 10.1021/bi048606d. PMID: 15518580.; Blume A, Ghaderi D, Liebich V, Hinderlich S, Donner P, Reutter W, Lucka L. UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase, functionally expressed in and purified from Escherichia coli, yeast, and insect cells. Protein Expression and Purification. 2004 Jun;35(2):387–96. doi: 10.1016/j.pep.2004.02.013.; Chou WK, Hinderlich S, Reutter W, Tanner ME. Sialic acid biosynthesis: stereochemistry and mechanism of the reaction catalyzed by the mammalian UDP-N-acetylglucosamine 2-epimerase. J Am Chem Soc. 2003 Mar 05;125(9):2455–61. doi: 10.1021/ja021309g. PMID: 12603133.; Stäsche R, Hinderlich S, Weise C, Effertz K, Lucka L, Moormann P, Reutter W. A bifunctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver. Molecular cloning and functional expression of UDP-N-acetyl-glucosamine 2-epimerase/N-acetylmannosamine kinase. J Biol Chem. 1997 Sep 26;272(39):24319–24. doi: 10.1074/jbc.272.39.24319. PMID: 9305888.

Metabolites

1,10-Phenanthroline

Formula: C12H8N2 (180.0687448)

CAS ID: 66-71-7

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

D-Mannose

Formula: C6H12O6 (180.0633852)

CAS ID: 3458-28-4

Diphosphate

Formula: H4P2O7 (177.9432294)

CAS ID: 2466-09-3

Dithiothreitol

Formula: C4H10O2S2 (154.01222)

CAS ID: 3483-12-3

Fe2+

Formula: Fe (55.934939)

CAS ID: 15438-31-0

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Hydroxylamine

Formula: NH3O (33.0214628)

CAS ID: 7803-49-8

Iodine

Formula: I2 (253.808954)

CAS ID: 7553-56-2

Magnesium cation

Formula: Mg (23.98505)

CAS ID: 22537-22-0

Manganese(2+)

Formula: Mn (54.938046)

CAS ID: 7439-96-5

Mercaptoethanol

Formula: C2H6OS (78.0139346)

CAS ID: 60-24-2

Mercury(2+)

Formula: Hg (201.970632)

CAS ID: 14302-87-5

N-Ethylmaleimide

Formula: C6H7NO2 (125.0476762)

CAS ID: 128-53-0

Nickel(2+)

Formula: Ni (57.935347)

CAS ID: 14701-22-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Semicarbazide

Formula: CH5N3O (75.04326)

CAS ID: 57-56-7

Silver

Formula: Ag (106.905095)

CAS ID: 7440-22-4

Sodium chloride

Formula: NaCl (57.958623)

CAS ID: 7647-14-5

Zinc cation

Formula: Zn (63.929145)

CAS ID: 23713-49-7

ammonium sulfate

Formula: H8N2O4S (132.0204768)

CAS ID: 7783-20-2

ATP(4-)

Formula: C10H12N5O13P3 (502.9644492)

CAS ID:

UDP(3-)

Formula: C9H11N2O12P2 (400.9787246)

CAS ID: 86527-70-0

ADP(3-)

Formula: C10H12N5O10P2 (424.0059412)

CAS ID:

N-bromosuccinimide

Formula: C4H4BrNO2 (176.9425384)

CAS ID: 128-08-5



Enzyme

EC Number name full name note
1.14.18.2 CMP-N-acetylneuraminate monooxygenase CMP-N-acetylneuraminate,ferrocytochrome-b5:oxygen oxidoreductase (N-acetyl-hydroxylating)
1.6.2.2 cytochrome-b5 reductase NADH:ferricytochrome-b5 oxidoreductase
2.5.1.132 3-deoxy-D-glycero-D-galacto-nonulopyranosonate 9-phosphate synthase phosphoenolpyruvate:D-mannose-6-phosphate 1-(2-carboxy-2-oxoethyl)transferase
2.5.1.57 N-acylneuraminate-9-phosphate synthase phosphoenolpyruvate:N-acyl-D-mannosamine-6-phosphate 1-(2-carboxy-2-oxoethyl)transferase
2.7.1.60 N-acylmannosamine kinase ATP:N-acyl-D-mannosamine 6-phosphotransferase
2.7.7.43 N-acylneuraminate cytidylyltransferase CTP:N-acylneuraminate cytidylyltransferase
3.1.3.29 N-acylneuraminate-9-phosphatase N-acylneuraminate-9-phosphate phosphohydrolase
3.2.1.183 UDP-N-acetylglucosamine 2-epimerase (hydrolysing) UDP-N-acetyl-alpha-D-glucosamine hydrolase (2-epimerising)


Proteins

Protein ID name full name
P13266 neuA N-acylneuraminate cytidylyltransferase