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Alanine Pyruvate Asparagine Aspartate OAA Krebs cycle Lysine a-Ketoglutarate Urea Glutamate Nucleotides Methionine Ornithine Homoserine Proline Threonine Urea Arginine Glutamine Histidine Tryptophan Nucleotides Amino sugars Isoleucine Creatine phosphate COOCOO-Glu COOa-Kg H-C-OH C=O H3N- C-H Pyr L-Alanine CH2OP CH3 CH3 3-PGA a-Kg COOCOO- Glu COOCO2 C=O H3N-C-H ATP, NH3 H N-C-H 3 CH2 CH2 CH2 L-Asparagine OAA COO- L-Aspartate COO C-NH2 O COOCOOGlu a-Kg H3N-C-H ATP, NH3 H3N-C-H C=O CH2 CH2 CH2 L-Glutamine CH2 CH2 CH2 L-Glutamate COOC-NH2 COOO COO- a-Kg Making Amino Acids from Glucose Glucose F-1,6BP COOH3N-C-H H Glycine G-3-P COOCOO- Glu a-Kg COOCOOH2O H-C-OH NAD+ C=O H3N-C-H H3N-C-H CH2OP CH2OP CH2OH CH2OP 3-PGA Serine-PO4 Pyruvate-PO4 Serine COO- COOH3N-C-H CH2 CH2 CHO- H3N-C-H NADPH CH2 Glu CH2 COOGlutamate semialdehyde PROLINE BIOSYNTHESIS H2C HC NADPH CH2 CH N COO1-Pyrroline carboxylic acid H2C CH2 H2 C CH COO- L-Proline N H OAA/Aspartate COOCOOCOO+ + + H3N-C-H ATP H3N-C-H NADPH H3N-C-H CH2 CH2 CH2 -AspartylCOOC~OPO3= CHO semialdehyde O L-Aspartate NADPH Aspartyl--PO4 Threonine COO+ H3N-C-H H-C-OH CH3 COO+ H3N-C-H Homoserine CH2 COO+ H3N-C-H CH2 CH2 Homocysteine SH CH2OH L-Methionine Methyl-THF B12 p646 Serine Homocysteine CH2 S CH2 H3N-CH COOCH3 CH2 C=O COO- a-ketobutyrate CH2 CH COOCystathionine + NH3 Cystathione -lyase CH2-SH CH COONH3+ L-Cysteine Amino Acid Derivatives Take home: Amino acid provide the carbon and nitrogen atoms that make up the structures of many biomolecules with diverse biological functions Hormones Neurotransmitters Pigments Heme Polyamines Creatine Nucleic Acids Coenzymes Hormones • • • • Epinephrine Auxin Ethylene Thyroxine Phenylalanine Tryptophan Methionine Tyrosine Neurotransmitters • • • • Norepinephrine Dopamine Serotonin GABA Phenylalanine Phenylalanine Tryptophan Glutamate Famous Decarboxylations HN H CH2-C-COON H NH3+ + CO2 HN L-Histidine + Histamine (A-CHOO!) H HO CH2-C-COO O2 NH3+ N CO2 L-Tryptophan CH2-CH2-NH3+ NH CH2-CH2-NH3+ N 5-hydroxytryptamine Serotonin COOH3N-C-H CH2 CH2 COO- L-Glutamate CO2 H H3N-C-H CH2 CH2 COO- -Aminobutyric Acid (GABA) Versatility of Glycine Serine Purine Ring Glutathione COO+ H3N-C-H H Heme Glyoxylate Creatine-PO4 Creatine Phosphate +NH O H2 N O-P~ H O 2 C N CH2-COOCH3 ARGININE Creatine-PO4 GLYCINE METHIONINE HO HO HO HO HO H CH2-C-COONH3+ Phenylalanine H CH2-C-COONH3+ Tyrosine H CH2-C-COONH3+ CO2 H CH2-C-H NH3+ L-DOPA Dopamine Catechol Catecholamine HO HO H CH2-C-H NH3+ Dopamine O2 HO HO H C-CH2-NH3+ OH Norepinephrine SAM HO HO H H C-CH2-N-CH3 OH Epinephrine (Adrenaline) COO – H3N-C-H CH2 COO – H3N-C-H CH2 CH2 – COO CH2 – COO COO – H3N-C-H H2C CH2 HC CH2 – COO CH2 H2C H2C CH N COO CH2 CH N COO H
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