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What's another name for tryptophan? Decoding the essential amino acid

4 min read

Over 95% of the body's tryptophan is metabolized through the kynurenine pathway, rather than the more popularly known serotonin pathway. While most people recognize it as a precursor to serotonin, few know its chemical identity or other aliases. So, what's another name for tryptophan and why does this essential amino acid have so many different designations?

Quick Summary

Tryptophan is also known by its abbreviations Trp and W, its systematic IUPAC chemical name, and the common form L-tryptophan. It is a vital essential amino acid for producing serotonin, melatonin, and niacin.

Key Points

  • Multiple Names: Tryptophan is known by its three-letter abbreviation Trp, its one-letter code W, its chemical name 2-Amino-3-(1H-indol-3-yl)propanoic acid, and its biologically active form, L-tryptophan.

  • Essential Amino Acid: Your body cannot produce tryptophan, so it must be obtained from dietary sources like poultry, nuts, cheese, and seeds.

  • Serotonin and Melatonin Precursor: Tryptophan is the precursor for serotonin, a key neurotransmitter for mood and appetite, which is then converted into the sleep hormone melatonin.

  • Niacin Production: The body can also use tryptophan to synthesize niacin, or vitamin B3, which is needed for energy metabolism.

  • Dominant Metabolic Route: Over 95% of tryptophan is broken down through the kynurenine pathway, which is involved in immune regulation and inflammation, rather than the serotonin pathway.

  • Supplement Caution: While L-tryptophan supplements are available, potential side effects and past contamination issues mean dietary intake is often recommended as the safest route.

  • Two Isomers: Tryptophan has L- and D-isomers; L-tryptophan is the biologically active form found in nature, while D-tryptophan is synthetic.

In This Article

Diverse Names for a Vital Nutrient

While "tryptophan" is the universally recognized term for this essential amino acid, it possesses several other names and designations used in scientific, medical, and nutritional contexts. These variations often refer to its chemical structure, its specific isomer, or its shorthand notation.

The Systematic IUPAC and Other Chemical Names

The most comprehensive name for tryptophan is its systematic IUPAC (International Union of Pure and Applied Chemistry) name, which precisely describes its molecular structure. This name is 2-Amino-3-(1H-indol-3-yl)propanoic acid. It is derived from the indole side chain and the propanoic acid backbone with an attached amino group. This chemical identifier is primarily used by chemists and researchers for precise identification.

Other less formal, but still chemically descriptive names include:

  • alpha-Amino-beta-(3-indolyl)-propionic acid
  • 3-Indol-3-ylalanine
  • L-β-3-indolylalanine

Common Abbreviations and Synonyms

In biochemistry and protein studies, tryptophan is often referred to by shorter codes for convenience. Its primary abbreviations are:

  • Three-letter code: Trp
  • One-letter code: W

This one-letter code was assigned based on the visual complexity of the bulky, double-ring structure, which resembles a 'W'. Synonyms used in different languages or contexts also exist, such as L-Tryptophane and Triptofano.

The "L" and "D" Isomers: L-Tryptophan and D-Tryptophan

Like many other amino acids, tryptophan exists in two isomeric forms that are mirror images of each other: L-tryptophan and D-tryptophan. While the L-isomer is the biologically active form found in proteins and foods, the D-isomer is produced synthetically or by microorganisms. Therefore, L-tryptophan is a very common alternative name for the dietary and supplemental form of the amino acid.

How Tryptophan Functions in the Body

Regardless of what we call it, tryptophan plays a foundational role in several critical physiological processes. Since it is an essential amino acid, it must be consumed through the diet, as the human body cannot synthesize it.

The Serotonin Pathway: Mood and Sleep

Tryptophan is the sole precursor for the neurotransmitter serotonin, often called the "happiness hormone". The body converts tryptophan into the intermediate 5-HTP, which is then converted into serotonin. Serotonin is vital for regulating mood, appetite, and sleep. Furthermore, serotonin is used to create the hormone melatonin, which helps regulate the sleep-wake cycle.

The Kynurenine Pathway: Immune Response and Inflammation

As mentioned in the introduction, the kynurenine pathway is the dominant route for tryptophan metabolism, accounting for over 95% of its degradation. This pathway produces numerous metabolites that are heavily involved in regulating the immune system and influencing inflammation. Imbalances in this pathway are linked to a wide range of neurological and psychiatric conditions.

Niacin Production: Energy and Metabolism

The liver can use tryptophan to produce niacin, also known as vitamin B3. Niacin is a crucial component of coenzymes NAD+ and NADP+, which are involved in over 250 redox reactions in the human body, including energy metabolism. A deficiency in niacin can lead to pellagra, a disease characterized by dermatitis, diarrhea, and dementia.

Sources and Supplementation

To ensure adequate intake, one can consume a variety of protein-rich foods. Common sources of tryptophan include:

  • Animal-based foods: Turkey, chicken, fish, cheese, milk, eggs, red meat.
  • Plant-based foods: Pumpkin and sesame seeds, nuts, tofu and soy products, oats, chocolate, potatoes.

While consuming these foods is the safest way to obtain tryptophan, supplements are also available. However, in the late 1980s, a tainted batch of L-tryptophan supplements led to a rare and dangerous condition called eosinophilia-myalgia syndrome (EMS). Although subsequent investigations traced the issue to a contaminant, not the tryptophan itself, the FDA still advises caution with supplementation. Some doctors may recommend 5-HTP supplements instead, as it is one step closer to serotonin synthesis.

A Look at L-Tryptophan vs. D-Tryptophan

Feature L-Tryptophan D-Tryptophan
Biological Activity Yes, the biologically active form. No, not naturally integrated into proteins.
Source Found naturally in dietary proteins. Produced synthetically or by microorganisms.
Metabolism Precursor to serotonin, melatonin, niacin, etc. Can be converted to L-tryptophan by some species, but less potent.
Commercial Use Commonly sold as a dietary supplement. Less common in supplements; used in research.
Human Use Used for mood, sleep support, and protein synthesis. Not typically used for nutritional purposes in humans.

Conclusion

In summary, there is no single answer to "what's another name for tryptophan?" The amino acid is known by several designations, from its clinical three-letter code "Trp" to its complex chemical identifiers like "2-Amino-3-(1H-indol-3-yl)propanoic acid." For most people, L-tryptophan is the most relevant alternative name, referring to the dietary form of this essential nutrient. Regardless of its name, its fundamental role in synthesizing critical compounds like serotonin, melatonin, and niacin underscores its importance for overall health and well-being. For those considering supplements, focusing on tryptophan-rich foods remains the safest and most effective way to maintain healthy levels.

For more detailed information on tryptophan's role in the body, you can refer to authoritative sources like the National Institutes of Health.(https://pmc.ncbi.nlm.nih.gov/articles/PMC6158605/)

Frequently Asked Questions

The systematic chemical name for tryptophan is 2-Amino-3-(1H-indol-3-yl)propanoic acid. This name provides a precise, standardized description of its molecular structure.

The three-letter abbreviation commonly used for tryptophan in biochemistry is Trp.

The one-letter code for tryptophan is W. The letter was chosen because the amino acid has the largest and most visually complex side chain.

The 'L' in L-tryptophan refers to the molecule's specific isomeric form. It is the biologically active version found in nature and utilized by the human body for protein synthesis and other functions.

L-tryptophan is the natural, biologically active isomer, while D-tryptophan is a synthetic, mirror-image version. Humans primarily use the L-form, though some species can metabolize the D-form.

Yes, tryptophane is an older or alternative spelling used in some contexts to refer to the same amino acid.

The body converts tryptophan into the intermediate 5-HTP (5-hydroxytryptophan), which is then converted into serotonin. Subsequently, serotonin is converted into melatonin in the pineal gland to regulate sleep.

References

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Medical Disclaimer

This content is for informational purposes only and should not replace professional medical advice.