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Is There Another Name for L-histidine? Synonyms and Chemical Nomenclature

4 min read

Over 75% of the body's 3-methylhistidine, a marker of myofibrillar protein degradation, is estimated to come from skeletal muscle. This highlights the deep chemical significance of amino acids and begs the question: is there another name for L-histidine?

Quick Summary

L-histidine is also known by its three-letter abbreviation His, its chemical name (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid, and older names like Glyoxaline-5-alanine.

Key Points

  • Abbreviation (His): The most common shorthand name for L-histidine is 'His,' widely used in biological and chemical contexts.

  • Chemical Name: L-histidine's precise IUPAC name is (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid, which describes its exact molecular structure.

  • Other Synonyms: It has various other scientific names, including Glyoxaline-5-alanine and the database identifier NSC 137773.

  • Semi-Essential Status: L-histidine is a semi-essential amino acid, meaning that while the body can produce some, it often relies on dietary sources, especially in children.

  • Precursor to Histamine: L-histidine is the direct precursor to the neurotransmitter histamine, which is involved in immune responses and other bodily functions.

  • Dietary Sources: Good sources include meat, fish, eggs, dairy, whole grains, nuts, and beans.

In This Article

The Significance of L-Histidine

L-histidine is one of the 22 proteinogenic amino acids, which means it is a building block for proteins in the body. While the body can't produce it entirely, making it 'semi-essential' for adults and essential for children, it plays a vital role in various biological functions. For instance, L-histidine is a precursor for histamine, a neurotransmitter that plays a crucial role in immune response, digestion, and sexual function. It is also critical for the growth and repair of body tissues and for maintaining the myelin sheaths that protect nerve cells. Its importance to human health makes a clear understanding of its identity, including its various names, highly relevant for anyone in the biochemical or nutritional fields.

Where L-Histidine Is Found

To meet the body's needs for L-histidine, it is primarily obtained through diet. It is present in many high-protein foods, demonstrating why a balanced diet is important for amino acid intake. Key dietary sources include:

  • Meat: Red meat and poultry are excellent sources.
  • Fish: Many varieties, especially certain dark muscle fish, contain high levels.
  • Eggs and Dairy: A significant source of histidine.
  • Grains and Nuts: Whole grains and various nuts provide plant-based sources.
  • Beans and Legumes: Another vital plant-based option.

Common and Chemical Names for L-Histidine

Yes, L-histidine is known by several other names, which can vary depending on context, such as a casual abbreviation, a precise chemical name used in a lab, or a historical synonym. Here are the most common alternatives:

  • His: This is the standard three-letter abbreviation for histidine, widely used in chemistry and biology to represent the amino acid.
  • H: The one-letter abbreviation for histidine, typically used in protein sequences.
  • (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid: This is the systematic IUPAC chemical name for L-histidine, providing a precise description of its molecular structure.
  • (S)-Histidine: Refers to the specific stereoisomer of histidine. The 'L' in L-histidine and 'S' (from the Cahn-Ingold-Prelog priority rules) are often used interchangeably to denote the biologically active form.
  • Glyoxaline-5-alanine: An older, less common name for histidine.
  • L-(-)-Histidine: The L- prefix combined with the direction of optical rotation, though modern nomenclature prefers the S- prefix for absolute configuration.
  • NSC 137773: A reference number assigned in the National Cancer Institute's database.

Historical Context of the Name 'Histidine'

Historically, the name 'histidine' was coined in 1896 by German biochemist Albrecht Kossel, referencing the Greek word 'histos,' meaning 'tissue'. This was because the substance was isolated from histones, which are basic proteins found in animal tissue. This gives insight into the historical process of biochemical discovery and naming conventions.

How Names Differentiate Histidine Forms

Understanding the context behind the different names for histidine is important. The name can specify a particular chemical property, like stereochemistry, or simply be a shorthand for convenience.

Naming Convention Example Context Purpose
Common Abbreviation His General lab research, protein sequence databases Simplicity and speed
Chemical Name (IUPAC) (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid Detailed chemical synthesis, publication Precision and clarity
Stereochemical Notation (S)-Histidine or L-Histidine Biochemical pathways, pharmacological studies Specifying biological activity
Database Identifier NSC 137773 Cataloging chemical properties and research Universal identification
Historical Name Glyoxaline-5-alanine Historical documents, older chemical literature Legacy reference

Comparison with D-Histidine

It is also worth noting the distinction between L-histidine and D-histidine. While they share the same chemical formula, they are different stereoisomers, or mirror images, of each other. The 'L' and 'D' prefixes refer to the spatial arrangement of atoms around the central carbon atom. L-amino acids are the forms typically found in proteins in living organisms, including humans. D-amino acids are much less common in biological systems but can exist. The different spatial orientation means they are not interchangeable and have different biological functions, making the inclusion of the 'L' prefix crucial in a biochemical context. The precision of the chemical name, such as including '(2S)', further specifies the exact molecular configuration.

The Role of Histidine in Human Health

Beyond its role as a protein building block, histidine performs several other crucial functions in the body. Its imidazole side chain, which can change its charge depending on pH, makes it particularly important in the active sites of many proteins, such as hemoglobin and myoglobin. In these proteins, it helps bind and transport oxygen in the blood. Histidine is also part of important dipeptides like carnosine, which acts as a buffer in muscles during exercise to prevent the buildup of lactic acid. This makes it a popular supplement for athletes. Furthermore, derivatives of histidine, such as 3-methylhistidine, are markers of protein turnover in the body.

Conclusion

To answer the question, is there another name for L-histidine, the answer is a definitive yes. The amino acid L-histidine goes by several names, from the common abbreviation 'His' to its precise IUPAC chemical name, (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid. Understanding these different names is important for navigating various scientific and nutritional contexts. Whether found in dietary sources like meat and fish or functioning within our hemoglobin to transport oxygen, L-histidine remains a fundamentally important semi-essential amino acid with a rich nomenclature. The next time you see 'His' on a biochemical chart or read a detailed chemical analysis, you'll know it's a reference to this versatile and vital compound. For more information on its metabolism and physiological functions, you can visit the NIH's article on histidine.

Frequently Asked Questions

The three-letter abbreviation commonly used for L-histidine in scientific and biochemical contexts is 'His'.

The systematic IUPAC chemical name for L-histidine is (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid, which precisely identifies its molecular structure.

Yes, in most biological discussions, 'histidine' refers to the L-stereoisomer (L-histidine), as it is the form found in proteins. The 'L' denotes the specific biologically active form.

The one-letter abbreviation for L-histidine, particularly in the context of protein sequencing, is 'H'.

Yes, older chemical and biochemical literature may refer to L-histidine as Glyoxaline-5-alanine. The name 'histidine' itself originates from the Greek 'histos,' meaning tissue.

The 'L' is crucial as it specifies the stereoisomer. The 'L' form is the one used to build proteins in the body, while the 'D' form, a mirror image, has different biological properties.

L-histidine has different names to serve various purposes, including scientific precision (chemical name), common usage (abbreviation), and historical context. Each name provides different information about the molecule.

References

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Medical Disclaimer

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