3Glucose-6-P 3Ru5P + Gln F6P + E4P + R5P 3PG NH3 + 2 PEP + E4P + R5P + Serine Tryptophan + pyruvate + GAP + CO2

Aldolase

2-keto-3-deoxy-arabinoheptulosonate-7-phosphate synthase

chorismate synthase

Phenylalanine Tyrosine Anthranilate Chorismate Prephenate p-hydroxybenzoate p-aminobenzoate Tryptophan Nictotinamide Phenylalanine Tyrosine Tetrahydrofolate Coenzyme Q

+

Ribose-5-phosphate Cost = 2 ATP

3 glucose + 5NADP+ + 2NAD+ + 2ATP serine + glutamine ---> Tryptophan + 5NADPH + 2NADH + 2ADP + 2Pi + GAP + pyruvate + 4CO2 + glutamate glutamine costs NADPH + 2NH4+ + 2ATP GAP + glutamate + ATP + 2NADH = serine 3 glucose + 4NADP+ + 2NH4+ + 4NAD+ + ADP + Pi ---> Tryptophan + 4NADPH + 4NADH + ATP + pyruvate + 4CO2

Chorismate mutase

prephenate

3 glucose + 2NAD+ + 4NADP+ + NH4+ + ATP ---> phenylalanine + R5P + 4NADPH + 2NADH + 4CO2 + ADP + Pi 3 glucose + 3NAD+ + 4NADP+ + NH4+ + ATP ---> tyrosine + R5P + 4NADPH + 3NADH + 4CO2 + ADP + Pi In animals tyrosine is made from phenylalanine by phenylalanine hydroxylase

Tyrosine production from phenylalanine

Tryptophan: indolamine-2,3-dioxygenase

N-formylkynurenine formamidase

N10-formyl-THF synthetase Loss of ATP! N10-formyl-THF

Kynurenine-3-hydroxylase (monooxygenase)

Kynurenine 3-hydroxykynurenine

Lose 1 NADPH!

Kynureninase

So…Trp = alanine - ATP - NADPH + 3-hydroxyanthranilate If: Ala = 13 ATP Then: Trp = 12 ATP - NADPH + 3-hydroxyanthranilate

3-hydroxyanthranilate dioxygenase 2-amino-3-carboxymuconate-6-semialdehyde 3-hydroxyanthranilate dioxygenase

If you need nictotinamide it ends here

Assume loss of NADH

Trp = 12 ATP - 2 NADPH - (NADH?) + NADH + -ketoadipate + NH3

-ketoadipate dehydrogenase Same mechanism as pyruvate dehydrogenase and -ketoglutarate dehydrogenase.

-ketoadipate = NADH + glutaryl-CoA

-ketoadipate = NADH + FADH2 + glutaconyl-CoA

-ketoadipate = 2 NADH + FADH2 + Acetoacetyl-CoA

-ketoadipate = 2 NADH + FADH2 + 2 Acetyl-CoA

So…Trp = 12 ATP - 2 NADPH + NH3+ -ketoadipate If: -ketoadipate = 2 NADH + FADH2 + 2 Acetyl-CoA If: Acetyl-CoA = 3 NADH + FADH2 + GTP Then: -ketoadipate = 8 NADH + 3 FADH2 + 2 GTP Then: Trp = 12 ATP + 8 NADH + 3 FADH2 + 2 GTP - 2 NADPH + NH3 Remember malate dehydrogenase + malic enzyme converts NADH + NADP+ ---> NAD+ + NADPH So….-2 NADPH = -2 NADH Then: Trp = 12 ATP + 6 NADH + 3 FADH2 + 2 GTP + NH3 If GTP = ATP, NADH = 3 ATP FADH2 = 2 ATP and NH3 = -2 ATP Then: Trp = 36 ATP + N10-formyl-THF

Tyrosine and phenylalanine degradation

Makes fumarate + acetoacetate at the expense of NADPH and ascorbate

So…Phe = fumarate + acetoacetate - NADPH - Asc + NH3 and Tyr = fumarate + acetoacetate - Asc + NH3 If: fumarate = malate Then: Phe = malate + acetoacetate - NADPH - Asc + NH3 and Tyr = malate + acetoacetate - Asc + NH3 If: malate = pyruvate - NADH + NADPH Then: Phe = pyruvate + acetoacetate - NADH - Asc + NH3 and Tyr = pyruvate + acetoacetate - Asc + NH3 - NADH + NADPH If: acetoacetate = 2 Acetyl-CoA - ATP Then: Phe = pyruvate + 2 Acetyl-CoA - NADH - Asc + NH3 -ATP and Tyr = pyruvate + 2 Acetyl-CoA - Asc + NH3 - NADH + NADPH - ATP If: pyruvate = 4 NADH + FADH2 + GTP If: Acetyl-CoA = 3 NADH + FADH2 + GTP Then: Phe = 9 NADH + 3 FADH2 + 2 GTP - Asc + NH3 and Tyr = NH3 + 2 GTP + 3 FADH2 + 9 NADH + NADPH - Asc

If GTP = ATP, NADH = 3 ATP FADH2 = 2 ATP and NH3 = -2 ATP Then: Phe = 9 NADH + 3 FADH2 + 2 GTP - Asc + NH3 and Tyr = NH3 + 2 GTP + 3 FADH2 + 9 NADH - NADPH - Asc If: Asc = - NADPH Then: Phe = 9 NADH + 3 FADH2 + 2 GTP - NADPH + NH3 and Tyr = NH3 + 2 GTP + 3 FADH2 + 9 NADH - 2 NADPH If: NADPH = NADH Then: Phe = 8 NADH + 3 FADH2 + 2 GTP + NH3 and Tyr = NH3 + 2 GTP + 3 FADH2 + 7 NADH If GTP = ATP, NADH = 3 ATP FADH2 = 2 ATP and NH3 = -2 ATP Then: Phe = 30 ATP Tyr = 27 ATP

Histidine degradation Ammonia lyase Urocanase Urocanase Urocanase Urocanase Urocanase

formiminotransferase Imidazolone propionase Glutamate formiminotransferase

So….Histidine = glutamate + N5-formimino-THF If: Glu = -ketoglutarate + NADPH + NH3 Then: His = -ketoglutarate + NADPH + NH3 If: -ketoglutarate = 4 NADH + 2 GTP + 2 FADH2 + NADPH Then: His = 4 NADH +2 GTP + 2 FADH2 + NADPH + NH3 If: NADH = 3 ATP GTP = ATP FADH2 = 2 ATP NH3 = -2 ATP Then: His = 16 ATP + NADPH + N5-formimino-THF

Amino acids as precursors for biological molecules