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Tryptophan (symbol Trp or W)^[2] is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a non-polar aromatic amino acid. It is essential in humans, meaning the body cannot synthesize it; it must be obtained from the diet. Tryptophan is also a precursor to the neurotransmitterserotonin, the hormonemelatonin and vitamin B3.^[3] It is encoded by the codon UGG.

Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–NH₃⁺; pK_a = 9.39) and the carboxylic acid is deprotonated ( –COO⁻; pK_a = 2.38).^[4]

• 2Recommended dietary allowance
• 8Society and culture
• 9Research

Function[edit]

Amino acids, including tryptophan, are used as building blocks in protein biosynthesis, and proteins are required to sustain life. Many animals (including humans) cannot synthesize tryptophan: they need to obtain it through their diet, making it an essential amino acid. Tryptophan is among the less common amino acids found in proteins, but it plays important structural or functional roles whenever it occurs. For instance, tryptophan and tyrosine residues play special roles in 'anchoring' membrane proteins within the cell membrane. In addition, tryptophan functions as a biochemical precursor for the following compounds:

• Serotonin (a neurotransmitter), synthesized by tryptophan hydroxylase.^[5][6]
• Melatonin (a neurohormone) is in turn synthesized from serotonin, via N-acetyltransferase and 5-hydroxyindole-O-methyltransferase enzymes.^[7]
• Niacin, also known as vitamin B₃, is synthesized from tryptophan via kynurenine and quinolinic acids.^[8]
• Auxins (a class of phytohormones) are synthesized from tryptophan.^[9]

The disorder fructose malabsorption causes improper absorption of tryptophan in the intestine, reduced levels of tryptophan in the blood,^[10] and depression.^[11]

In bacteria that synthesize tryptophan, high cellular levels of this amino acid activate a repressor protein, which binds to the trp operon.^[12] Binding of this repressor to the tryptophan operon prevents transcription of downstream DNA that codes for the enzymes involved in the biosynthesis of tryptophan. So high levels of tryptophan prevent tryptophan synthesis through a negative feedback loop, and when the cell's tryptophan levels go down again, transcription from the trp operon resumes. This permits tightly regulated and rapid responses to changes in the cell's internal and external tryptophan levels.

Recommended dietary allowance[edit]

In 2002, the U.S. Institute of Medicine set a Recommended Dietary Allowance (RDA) of 5 mg/kg body weight/day of Tryptophan for adults 19 years and over.^[17]

Dietary sources[edit]

Tryptophan is present in most protein-based foods or dietary proteins. It is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Contrary to the popular belief^[18][19][20] that cooked turkey contains an abundance of tryptophan (with this being used as an explanation for sleepiness following consumption of the meat), the tryptophan content in turkey is typical of poultry.^[21]

Use as a dietary supplement[edit]

Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed that consumption of tryptophan or 5-HTP may improve depression symptoms by increasing the level of serotonin in the brain. Tryptophan is sold over the counter in the United States (after being banned to varying extents between 1989 and 2005) and the United Kingdom as a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. It is also marketed as a prescription drug in some European countries for the treatment of major depression. There is evidence that blood tryptophan levels are unlikely to be altered by changing the diet,^[23][24] but consuming purified tryptophan increases the serotonin level in the brain, whereas eating foods containing tryptophan does not.^[25] This is because the transport system that brings tryptophan across the blood–brain barrier also transports other amino acids which are contained in protein food sources.^[26] High blood plasma levels of other large neutral amino acids prevent the plasma concentration of tryptophan from increasing brain concentration levels.^[26]

In 2001 a Cochrane review of the effect of 5-HTP and tryptophan on depression was published. The authors included only studies of a high rigor and included both 5-HTP and tryptophan in their review because of the limited data on either. Of 108 studies of 5-HTP and tryptophan on depression published between 1966 and 2000, only two met the authors' quality standards for inclusion, totaling 64 study participants. The substances were more effective than placebo in the two studies included but the authors state that 'the evidence was of insufficient quality to be conclusive' and note that 'because alternative antidepressants exist which have been proven to be effective and safe, the clinical usefulness of 5-HTP and tryptophan is limited at present'.^[27] The use of tryptophan as an adjunctive therapy in addition to standard treatment for mood and anxiety disorders is not supported by the scientific evidence.^[27][28]

Side effects[edit]

Potential side effects of tryptophan supplementation include nausea, diarrhea, drowsiness, lightheadedness, headache, dry mouth, blurred vision, sedation, euphoria, and nystagmus (involuntary eye movements).^[29][30]

Interactions[edit]

Tryptophan taken as a dietary supplement (such as in tablet form) has the potential to cause serotonin syndrome when combined with antidepressants of the MAOI or SSRI class or other strongly serotonergic drugs.^[30] Because tryptophan supplementation has not been thoroughly studied in a clinical setting, its interactions with other drugs are not well known.^[27]

Isolation[edit]

The isolation of tryptophan was first reported by Frederick Hopkins in 1901.^[31] Hopkins recovered tryptophan from hydrolysedcasein, recovering 4–8 g of tryptophan from 600 g of crude casein.^[32]

Biosynthesis and industrial production[edit]

As an essential amino acid, tryptophan is not synthesized from simpler substances in humans and other animals, so it needs to be present in the diet in the form of tryptophan-containing proteins. Plants and microorganisms commonly synthesize tryptophan from shikimic acid or anthranilate:^[33] anthranilate condenses with phosphoribosylpyrophosphate (PRPP), generating pyrophosphate as a by-product. The ring of the ribosemoiety is opened and subjected to reductive decarboxylation, producing indole-3-glycerol phosphate; this, in turn, is transformed into indole. In the last step, tryptophan synthasecatalyzes the formation of tryptophan from indole and the amino acid serine.

The industrial production of tryptophan is also biosynthetic and is based on the fermentation of serine and indole using either wild-type or genetically modified bacteria such as B. amyloliquefaciens, B. subtilis, C. glutamicum or E. coli. These strains carry mutations that prevent the reuptake of aromatic amino acids or multiple/overexpressed trp operons. The conversion is catalyzed by the enzyme tryptophan synthase.^[34][35][36]

Society and culture[edit]

Eosinophilia–myalgia syndrome[edit]

There was a large outbreak of eosinophilia-myalgia syndrome (EMS) in the U.S. in 1989, with more than 1,500 cases reported to the CDC and at least 37 deaths.^[37] After preliminary investigation revealed that the outbreak was linked to intake of tryptophan, the U.S. Food and Drug Administration (FDA) recalled tryptophan supplements in 1989 and banned most public sales in 1990,^[38][39][40] with other countries following suit.^[41][42]

Subsequent studies suggested that EMS was linked to specific batches of L-tryptophan supplied by a single large Japanese manufacturer, Showa Denko.^{[38][43][44][45]} It eventually became clear that recent batches of Showa Denko's L-tryptophan were contaminated by trace impurities, which were subsequently thought to be responsible for the 1989 EMS outbreak.^[38][46][47] However, other evidence suggests that tryptophan itself may be a potentially major contributory factor in EMS.^[48]

The FDA loosened its restrictions on sales and marketing of tryptophan in February 2001,^[38] but continued to limit the importation of tryptophan not intended for an exempted use until 2005.^[49]

The fact that the Showa Denko facility used genetically engineered bacteria to produce the contaminated batches of L-tryptophan later found to have caused the outbreak of eosinophilia-myalgia syndrome has been cited as evidence of a need for 'close monitoring of the chemical purity of biotechnology-derived products'.^[50] Those calling for purity monitoring have, in turn, been criticized as anti-GMO activists who overlook possible non-GMO causes of contamination and threaten the development of biotech.^[51]

Turkey meat and drowsiness[edit]

A common assertion in the US is that heavy consumption of turkey meat results in drowsiness, due to high levels of tryptophan contained in turkey.^[18][20] However, the amount of tryptophan in turkey is comparable to that contained in other meats.^[19][21]Drowsiness after eating may be caused by other foods eaten with the turkey, particularly carbohydrates.^[52] Ingestion of a meal rich in carbohydrates triggers the release of insulin.^{[53][54][55][56]} Insulin in turn stimulates the uptake of large neutral branched-chain amino acids (BCAA), but not tryptophan, into muscle, increasing the ratio of tryptophan to BCAA in the blood stream. The resulting increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAA and aromatic amino acids), resulting in more uptake of tryptophan across the blood–brain barrier into the cerebrospinal fluid (CSF).^[56][57][58] Once in the CSF, tryptophan is converted into serotonin in the raphe nuclei by the normal enzymatic pathway.^[54][59] The resultant serotonin is further metabolised into melatonin by the pineal gland.^[7] Hence, these data suggest that 'feast-induced drowsiness'—or postprandial somnolence—may be the result of a heavy meal rich in carbohydrates, which indirectly increases the production of melatonin in the brain, and thereby promotes sleep.^{[53][54][55][59]}

Research[edit]

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In 1912 Felix Ehrlich demonstrated that yeast attacks the natural amino acids essentially by splitting off carbon dioxide and replacing the amino group with hydroxyl. By this reaction, tryptophan gives rise to tryptophol.^[60]

Tryptophan affects brain serotonin synthesis when given orally in a purified form and is used to modify serotonin levels for research.^[25] Low brain serotonin level is induced by administration of tryptophan-poor protein in a technique called 'acute tryptophan depletion'.^[61] Studies using this method have evaluated the effect of serotonin on mood and social behavior, finding that serotonin reduces aggression and increases agreeableness.^[62]

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Fluorescence[edit]

Tryptophan is an important intrinsic fluorescent probe (amino acid), which can be used to estimate the nature of the microenvironment around the tryptophan residue. Most of the intrinsic fluorescence emissions of a folded protein are due to excitation of tryptophan residues.

See also[edit]

• 5-Hydroxytryptophan (5-HTP)

References[edit]

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    Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease
    Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
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    IPA metabolism diagram
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    Origin: • Endogenous • Microbial
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Further reading[edit]

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• Wood RM, Rilling JK, Sanfey AG, Bhagwagar Z, Rogers RD (May 2006). 'Effects of tryptophan depletion on the performance of an iterated Prisoner's Dilemma game in healthy adults'. Neuropsychopharmacology. 31 (5): 1075–84. doi:10.1038/sj.npp.1300932. PMID16407905.
• Sturtz R (2009). 'what is the difference between L-Tryptophan and 5-HTP?'. The Lidtke Letter: 1.

External links[edit]

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• 'KEGG PATHWAY: Tryptophan metabolism - Homo sapiens'. KEGG: Kyoto Encyclopedia of Genes and Genomes. 23 August 2006. Retrieved 20 April 2008.
• G. P. Moss. 'Tryptophan Catabolism (early stages)'. Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Archived from the original on 13 September 2003. Retrieved 20 April 2008.
• G. P. Moss. 'Tryptophan Catabolism (later stages)'. Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Archived from the original on 13 September 2003. Retrieved 20 April 2008.
• B. Mikkelson; D. P. Mikkelson (22 November 2007). 'Turkey Causes Sleepiness'. Urban Legends Reference Pages. Snopes.com. Retrieved 20 April 2008.

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• 14k Gold Black Diamond Engagement Ring / Unique Sunflower Wedding Ring / Flower Engagement Ring / Sunflower Ring / Floral Black Diamond Ring

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• Keep Fu**ing Going SunFlower Necklace You Are My Sunshine SunFlower Necklace Sunflower Jewelry Custom Sunflower Necklace

  €17.18€28.63€28.63 (40% off)

  FREE shipping

• navy blue tie with sunflower design with signature floral design to the rear by Frederick Thomas FT3230

  €23.55 Bestseller

• Sunflower Shoes, Sunflower, Custom Shoes, Custom Sneakers, Sneakers, Custom Nike, Custom Nikes, Custom Air Force 1, Nike Air force 1, Nike

  €162.27 Bestseller

• Tiny Sunflower In A Bottle With Personalised Message - sunflower birthday card - get well soon card - mother's day gift - sunshine card

  €13.55

• sunflowers card - sunflowers - floral greeting card - any occasion card - nature card - sunflower field - personalised card

  €3.24

• Sunflower, Flower, Good Luck, Keepsake, Stone, Gift, Present, Momento, Best Friends, Mummy, Mum, Grandparents, Granny, Grandma, Unique, Cute

  €5.89

  Only 3 available and it's in 9 people's carts

• Cabochon templates 'Colorful Autumn', digital, 24 motifs, hedgehog, squirrel, sunflower, pumpkin, mushrooms, in a size of your choice

  €3.59 FREE shipping

• 3.00 EUR/pc sliding pearl with Rivoli sunflower 12 mm (ID 10 x 2 mm) in rose gold for flat leather and ribbons SL1122MM12292RG

  €3.00

• 5.00 EUR/pc. Hook closure Rivoli sunflower 12 mm (ID 10x2) rose gold for flat leather and ribbons ZM0210RG292

  €5.00

• 10 pieces - sunflower pendant - silver

  €3.49

  Only 3 left

• Lovely Personalised Handmade 3D Pink Car with flowers Birthday Card. Any age. Daughter Niece Granddaughter Sister Friend

  €4.71 Bestseller

• Sunflower Necklace, Charm Necklace, Stainless Steel Necklace, Flower Charm, Custom Gift, Best Friend, Flower,Initial Charm,Personalized Gift

  €14.32 Bestseller

• Let Love Grow, Seed Packets, Wedding Favors, Thank You Favors, Sunflower Seed Packets, Wedding Seed Packets, Seed Packet Favors, With Seeds

  €33.42 Bestseller

• Sunflower Wall Art Sunflower Wall Decor Sunflower Canvas Sunflower Decor Sunflower Home Decor Sunflower Photo Sunflower Posters Flower Print

  €66.83

  Only 1 available and it's in 6 people's carts

• Sunflower TShirt - Wild and Free Shirt - Flower Tee - She is Life Itself Wild and Free - Plus Size Available - Women's Unisex

  €23.86

• Sunflower printed neck strap lanyard 20mm

  €2.93

• Silver sunflower charm choker on black cord with adjustable sliding knots by Serenity Project

  €3.48 Bestseller

• Autumn wreath ,Sunflower Berry Pumpkin Acorns wreath Front Door wreath Autumn decor Wreath with leaves Rustic wreath autumn wreath

  €29.22 Bestseller

• Sunflower Keyring Gift with optional heart tag. Cheerful positive quote keyring key chain.

  €11.78

  Only 3 available and it's in 5 people's carts

• Yellow Sunflower illustration wall art print - A4 / A3 art print - Bright Floral wall art Print - Gift for the home by Katy Pillinger

  €16.50

• Edible Yellow Sunflowers and Leaves. Edible Sugar Paste Sunflowers. Edible Wedding Flowers. Edible Yellow Flowers.

  €10.49 Bestseller

• navy blue tie with sunflower design with signature floral design to the rear by Frederick Thomas FT3230

  €23.55 Bestseller

• Sunflower Makeup Bag, Wash/Toiletry Bag, Sunflower Accessory Bag

  €11.78

• Flower Necklace, Sunflower Necklace, Sunflower Jewelry, Sunflower Gift, Bridesmaid Necklace, Gift for her, Sunflower Pendant, Charm Necklace

  €7.59 Bestseller

• Emma - Sunflower Wedding Invitation Set Templates, Sunflower Wedding Programs, Rustic Wedding Printables, Wedding Invitation Templett Set

  €93.49

• Beautiful sunflower theme natural topaz and natural diamond engagement ring /14k solid gold/925 sterling silver

  €143.23€238.71€238.71 (40% off)

  FREE shipping

• Rustic Sunflower Wedding Invitation Burgundy Cranberry Floral Sunflowers Wedding Customized Invite Set SC832(120LB premium card stock)

  €0.74€0.93€0.93 (20% off)

• 1.50 EUR/pc Zamak sliding bead (ID 5 x 2 mm) with flatback Sunflower 7 mm for leather & ribbons up to 5 x 2 mm

  €1.50

• Custom Sunflower Shoes, handpainted flower converse, Sunflower vans, floral shoes, Sunflower Converse

  €37.24 Bestseller

• Sunflower phone case for iPhone, SAMSUNG and HUAWEI M110

  €9.99 FREE shipping

• 2 set garden stick 'Sunflower' Edelrust

  €12.90

• Sunflower Atlanta (30 grains)

  Sold

• Fused Glass Hanging Heart With A Cat And Sunflowers Valentine's Day Mother's Day Gift Sun Catcher Present

  €11.78

  Only 2 available and it's in 3 people's carts

• Sunflowers, Folding card/3d card/pop-up

  €5.90

• LIVE Perennial, oxeye sunflower, Heliopsis Pers, Гелиопсис подсолнечниковидный

  €9.75

• Hand Painted Wine Glasses Sunflower Wedding Wine Glasses for Bridal shower Sunflower Mother's Day Gift Sunflower Birthday Gift Floral Glass

  €21.95

• Leather Sunflower Preserved Flower Box for Wife Girlfriend Women Mother's Day Gift, Leather 3rd Anniversary Gift, Personalized Gifts

  €95.47€112.32€112.32 (15% off)

  FREE shipping

• Mother of the Bride Gift Wedding Handkerchief, Printed Handkerchief, Wedding Gift to Mother, Personalized Gift, Sunflower

  €17.18

• Sunflower Necklace, Silver Sunflower Charm, Flower Sunflower Jewelry, Personalized Gifts, N1535

  €16.23 Bestseller

• sunflower wedding countdown block, days until wedding, rustic wedding countdown, personalised wedding countdown, engagement gift.

  €11.78

• Edible Yellow Sunflowers and Leaves. Edible Yellow Flowers. Edible Yellow Daisies. Edible flowers & Leaves. Sugar Paste Flowers.

  €14.02 Bestseller

• Black pithy sunflower (30 seeds)

  €2.00

  Only 3 left

• Pond decoration ceramic swimming blossom poppy or sunflower

  €18.50 FREE shipping

• Dwarf Sunflower Seeds, Mini Sunflowers from Heirloom seeds for your garden - 20 Seeds

  €2.99 FREE shipping

• Sunflower (D), Flower Child, Seasonal Summer, Autumn, Felt Dolls, Decoration, Seasons Decoration,

  €11.00

  Only 1 available and it's in 1 person's cart

• Sunflower // Vinyl sticker

  €3.85

• PunchIng Stencil Cutting Scrapbooking Card Making Big Shot Sunflower

  €7.99

  Only 2 available and it's in 1 person's cart

• infant urn with name, date. Optional gold upgrade shown

  €119.35

• Sunflower Locket Nature Inspired Gift Silver Sunflower Flower Necklace Garden Flower Handmade Keepsake Locket Bohemian Girlfriend Gift

  €27.50€30.55€30.55 (10% off)

• Sunflower Garden Large Canvas Original Painting -24x36 - Ready to Ship

  €272.13

• For you..

  €33.42

• Flower Wooden Keyring, gardeners gift, birthday gift, stocking filler, dandelion, sunflower, cyclamen

  €4.12

• Sunflower sepals veiners, polymer clay, cold porcelain, Sugarcraft shapes, modelling mass, cake decor, sugar flowers, silicone moulds

  €2.50

• Sunflower Fabric No. 170265

  €9.80

• Sunflower Tote Bag Eco Tote Bag Floral Illustration Eco Friendly Shopper Botanical Illustration Canvas Tote Bag Floral Tote Bag

  €5.89 Bestseller

• Long-stemmed felted sunflowers for the vase, as a birthday present for the mother or as a home decoration

  €14.50

• On-iron patch ironing pattern embroidered sunflower yellow sequined flower

  €3.00 FREE shipping

• Gustav Klimt - Farm Garden with Sunflowers (1906) - Reproduction of a Classic Painting - Photo Poster Print Art Gift

  €7.66

• Sunflower Hanging slate heart,/unique gift/personalised gift/wall decor,home decor/wall art/kitchen decor

  €14.14 FREE shipping

• Sunflowers oil painting unique one-of-a-kind wall art decor. Bright sunflowers in a purple vase on canvas, 18x24 inches

  €238.70

• Sunflower Necklace, Sun Flower Charm Necklace, Flower Necklace, Personalized, Monogram Initial Necklace, Sunflower Pendant Necklace Y412

  €16.22

• Personalized Sunflower Necklace

  €11.94

• Faux Wood & Sunflower Birthday Personalized Waterproof Water Bottle Labels

  €15.75

• 3rd wedding anniversary card - leather - 3rd anniversary - three years - sunflower- teddy bear

  €6.48

  Only 1 available and it's in 4 people's carts

• Silver Sunflower Charm Necklace, Flower Charm Pendant, Gift For Her

  €11.78

• Birthday card 'Sunflower'

  €2.00

• Sunflower - Mini

  €1.95

• sunflower child for your natural table waldorf, harvesttime, autumn

  €12.00

• Sunflower leaf veiner, polymer clay, cold porcelain, Sugarcraft shapes, modelling mass, cake decor, sugar flowers, silicone moulds

  €6.50

• Artificial fake Sunflower Bouquet Plant Fake Flowers Garden Decoration Material Home Party Sunlight Plant Accessories Sunflower

  €16.70€20.87€20.87 (20% off)

  FREE shipping

• Enamel cup - Sunflower

  €15.00

• Sunflower Kitchen, Sunflower Art Poster, Old Botanical Print, Sunflower Home Decor, Old Sunflower Print, Mother Gift Decor E14_8

  €5.10€6.00€6.00 (15% off)