Vitamins – Chemistry – Flashcards

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Hormone precursors:
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Vitamin D
Vitamin A
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Redox cofactors &/or antioxidants:
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Vitamin C
Vitamin E (tocopherols)
Vitamin K (phylloquinone, not
an antioxidant)
Vitamin B3 (Niacin)
Vitamin B2 (Riboflavin)
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Group transfer agents:
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Vitamin B6
Vitamin B12
Biotin
Folic acid
Pantothenic acid
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formed in skin from 7-dehydrocholesterol plus sunlight
converted in the liver to a hormone that regulates calcium uptake.
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Vitamin D
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-family of is fat-soluble compounds
-found in fish oils, liver, eggs, whole milk, and butter
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Vitamin A
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________ (found in orange & yellow vegetables), can be enzymatically converted to Vitamin __
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Beta-carotene; A
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Deficiency - dryness of the skin, eyes, & mucous membranes, retarded growth, night blindness
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Vitamin A
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Deficiency is the leading cause of preventable blindness in children
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Vitamin A
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___________, one form of Vitamin A, functions as a hormone and as a pigment in the eye
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Retinol
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________ ________ - active drug in Retin-A used in the treatment of severe acne and other skin problems
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Retonoic Acid
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___ - ___ - ________ is a cofactor for rhodopsin, playing a role in vision
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11-cis-retinol
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What is the technical name for too much Vitamin A and D?
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hypervitaminosis A/D
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prevents free radicals (i.e. superoxide anions) from oxidizing compounds (i.e. polyunsaturated fats), thus maintaining integrity of cellular membranes
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Vitamin E, C
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found in eggs and vegetable oils
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Vitamin E
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Deficiency is very rare in humans; primary symptom is fragile erythrocytes, atherosclerosis, cardiovascular disease
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Vitamin E
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phylloquinone
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Vitamin K
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blood-clotting cofactor
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Vitamin K
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undergoes redox rxn to form prothrombin
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Vitamin K
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found in green plant leaves; deficiency is very rare.
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Vitamin K
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_______ (coumadin), with a similar structure, is used to prevent excessive blood clotting.
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Warfarin
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Isoprenoids = __ linear carbons, __ carbon off to the side
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4;5
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Vitamins __ and __ are isoprenoid derivatives
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E;K
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__________ (also called coenzyme Q) is an isoprenoid
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Ubiquinone
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Comes in three flavors: reduced, oxidized, ionized
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Vitamin C
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regenerates vitamin E from its radical form
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Vitamin C
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Most animals make vitamin __, but humans can’t; we obtain it through fruits & vegetables
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C
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required for the hydroxylation of proline in collagen (cofactor for prolyl 4-hydroxylase)
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Vitamin C
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What is Vitamin C in oxidized form?
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Dehydroascorbic Acid
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What is the reduced form of Vitamin C?
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Ascorbic Acid
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What is the ionized form of Vitamin C?
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Ascorbate
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Scurvy from _________ deficiency
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ascorbate
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__-_____________ required in collagen (connective tissue in
vertebrates)
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4 - hydroxyproline
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Deficiency of vitamin __ causes scurvy, characterized by _______ __________ degradation
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C; connective tissue degradation
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Poor healing, bleeding, tooth loss, bone pain, heart failure
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Vitamin C
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Milder cases: fatigue, irritability, increased severity of respiratory tract infections
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Vitamin C
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Cofactor for pyruvate & alpha-ketoglutarate dehydrogenase; hence, important for metabolism
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Vitamin B1- thiamine
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Also does Aldehyde transfers
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B1- thiamine
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Deficiency causes Beriberi – characterized by heart failure, peripheral neuropathy, Wernicke-Korsakoff syndrome (alcoholics-ataxia, ophthalmoplegia, confusion)
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B1- thiamine
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Activates Vitamin B6 (pyridoxine)
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B2- Riboflavin
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Involved in many oxidation-reduction reactions
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B2- Riboflavin, B3- Niacin
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Required for metabolism of amino acids, fatty acids, and carbohydrates
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B2- Riboflavin
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Found in meats, nuts, cheese, milk, leafy vegetables, fish, legumes, grains
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B2- Riboflavin
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Not toxic in high doses (but turns urine dark yellow)
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B2- Riboflavin
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Deficiency (not common) causes eye & skin problems, mouth inflammation
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B2- Riboflavin
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_______ is synthesized from tryptophan
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Niacin
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But humans generally cannot synthesize enough.
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B3- Niacin
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Deficiency affects all of the NAD(P)-dependent dehydrogenases, causing pellagra
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B3- Niacin
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___________ is characterized by the four D's =diarrhea, dermatitis, dementia, and death, from what deficiency?
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Pellagra; B3-Niacin
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100 years ago, when corn was a dietary
staple, pellagra was common because
corn is low in ______________.
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tryptophan
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What is pellagra commonly seen in today?
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alcoholics who have reduced niacin absorption
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____-_______ medicine can cause niacin
deficiency.
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Anti-tuberculoid
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_____ is synthesized from Niacin: no niacin = no ____
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NAD+; NAD+
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helps maintain healthy nerve and red blood cells
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B12- cobalamin
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found in fish, meat, poultry, eggs, milk, milk products
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B12- cobalamin
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Vegetarians & vegans are in danger of deficiency
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B12-cobalamin
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___ deficiency results in reduced levels of hemoglobin (megaloblastic anemia), as well as nervous system impairment that may be irreversible
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B12-cobalamin;
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______ ______ can correct the anemia from B12 deficiency, but not nerve damage.
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Folic Acid
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has a weak cobalt-carbon bond
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B12-Cobalamin
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organometallic biological molecule
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B12-Cobalamin
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Corrin ring structure: tetrapyrrole (4 heterocyclic aromatic rings) ring system
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B12- Cobalamin
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With 5'-deoxy-adenosine bound to cobalt, is called coenzyme B12.
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B12- Cobalamin
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Needed for more than 100 enzymes that play roles in protein metabolism (aids in group transfers to & from animo acids)
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B6- Pyridoxine
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enzyme cofactor _______ ________ is derived from vitamin B6
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pyridoxyl phosphate (PLP)
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Deficiency can result in anemia but is rare
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B6- Pyridoxine
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Found in a wide variety of foods
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B6-Pyridoxine, B7- Biotin
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Precursor to Coenzyme A, a carrier of carbon fragments such as acetate (i.e. acetyl-CoA); acyl transfers
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B5- Pantothenic Acid
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Found in many foods; deficiency not seen
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B5- Pantothenic Acid
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Deficiency is rare, but can result from a diet rich in raw eggs, because eggs are rich in avidin, which binds biotin very tightly
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B7- Biotin
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Deficiency also can be caused by longterm antibiotic use (synthesized in GI tract)
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B7-Biotin
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Carboxylizes pyruvate (to form oxaloacetate), acetyl CoA, and propionyl CoA; hence, necessary for Krebs Cycle
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B7-Biotin
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The _______ ________ derivative, tetrahydrofolate, carries 1-carbon units (more reduced form of CO2)
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Folic Acid
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Deficiency can stop DNA synthesis, also can cause megaloblastic anemia
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B9-Folic Acid
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_______ _______ is found in leafy vegetables, beans and peas.
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Folic Acid
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Grains are now (since 1996) enriched with _______ ______.
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Folic Acid
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Prevents neural tube defects in the developing fetus, and heart disease
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Folic Acid
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phototransduction
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Retinol; Vitamin A
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Carbohydrate Metabolism
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Thiamine B1
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redox, respiration
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Riboflavin B2
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redox
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niacin B3
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TCA, FA, and cholesterol
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Pantothenic Acid B5
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aa metabolism, glycogenolysis
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B6; pyridoxal, pyridoxamine, pyridoxine
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gluconeogenesis, fa, tca, aa
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Biotin B7
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1 C metabolism
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B9 Folic Acid
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hydroxylation
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ascorbic Acid
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component of oxidases in oxidative metabolism, neurotransmitter synthesis, collagen synthesis (deficiency = muscle weakness, neurological deficit, abnormal collagen)
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Copper
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essential component of thyroid hormone (deficiency =goiter, hypothyroidism)
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Iodine
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essential component of hemoglobin, other metallo-enzymes (deficiency = defective hemoglobin, anemia)
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Iron
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component of glutathione peroxidase (deficiency = cardiomyopathy)
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Selenium
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component of oxidases (deficiency = retarted growth & impaired wound healing)
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Zinc
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