What is the Difference Between N-Acetyl-D-Glucosamine and N-Acetyl Glucosamine

The key difference between N-acetyl-D-glucosamine and N-acetyl glucosamine is that N-acetyl-D-glucosamine is the D isomer of N-acetyl glucosamine, whereas N-acetyl glucosamine is an amide that occurs as a major component in the bacterial cell wall.

N-acetyl glucosamine is an important amide compound. It has two major isomers as, the D isomer and the L isomer. The D isomer is the most common and abundant form, while the L isomer is comparatively less abundant.

CONTENTS

1. Overview and Key Difference
2. What is N-Acetyl-D-Glucosamine 
3. What is N-Acetyl Glucosamine
4. Similarities – N-Acetyl-D-Glucosamine and N-Acetyl Glucosamine
5. N-Acetyl-D-Glucosamine vs N-Acetyl Glucosamine in Tabular Form
6. Summary – N-Acetyl-D-Glucosamine vs N-Acetyl Glucosamine 

What is N-Acetyl-D-Glucosamine?

N-acetyl-D-glucosamine is an isomer of N-acetyl glucosamine. It is one of two stereoisomers. The opposite isomer is N-acetyl-L-Glucosamine. Both N-acetyl-D-glucosamine and N-acetyl-L-glucosamine can contribute to the building of chitin. Moreover, it plays an important role as a bacterial metabolite. We can find it as a natural product that occurs in Daphnia pulex, Strept omyces alfalfa, etc.

What is N-Acetyl Glucosamine?

N-acetyl glucosamine is an amide that is derived from monosaccharide glucose. We can name it as a secondary amide formed from glucosamine and acetic acid. This substance is important for many biological systems. The chemical formula of this compound is C8H15NO6.

N-acetyl glucosamine can be found as a biopolymer in the bacterial cell wall. We can easily abbreviate the name of this substance as GlcNAc. It is the monomeric unit of the polymer chitin. Chitin forms the exoskeleton of anthropods such as insects and crustaceans. Chitin is the major component of the radulas of mollusks, the beaks of cephalopods, and it is a major component of the cell walls of most fungi. Moreover, upon the polymerization of N-acetyl glucosamine with glucuronic acid, it can produce hyaluronan.

Furthermore, N-acetyl glucosamine is considered an inhibitor of elastase that is released from human polymorphonuclear leukocytes. But this is weaker than the inhibition that can be observed in N-acetylgalactosamine.

When considering the medical uses of N-acetyl glucosamine, it is useful as a treatment for autoimmune diseases; some recent research studies have shown that this use has some success.

The addition of N-acetyl glucosamine to the serine or threonine of a protein is named as O-GlcNAcylation. This occurs by means of activating or deactivating enzymes or transcription factors.

What are the Similarities Between N-Acetyl-D-Glucosamine and N-Acetyl Glucosamine?

1. N-acetyl-D-glucosamine and N-acetyl glucosamine are important in building up the structure of the cell wall of bacterial cells.
2. Both N-acetyl-D-glucosamine and N-acetyl glucosamine show stereoisomerism.

What is the Difference Between N-Acetyl-D-Glucosamine and N-Acetyl Glucosamine?

N-acetyl-D-glucosamine is an isomer of N-acetyl glucosamine, while N-acetyl glucosamine is an amide that is derived from monosaccharide glucose. The key difference between N-acetyl-D-glucosamine and N-acetyl glucosamine is that N-acetyl-D-glucosamine is the D isomer of N-acetyl glucosamine, whereas N-acetyl glucosamine is an amide that occurs as a major component in the bacterial cell wall. Moreover, N-acetyl-D-glucosamine is highly abundant whereas the L isomer of N-acetyl glucosamine is less abundant while the D isomer is highly abundant.

Below is a summary of the difference between N-acetyl-D-glucosamine and N-acetyl glucosamine in tabular form for side by side comparison.

Summary – N-Acetyl-D-Glucosamine vs N-Acetyl Glucosamine

N-acetyl-D-glucosamine is an isomer of N-acetyl glucosamine, while N-acetyl glucosamine is an amide that is derived from monosaccharide glucose. The key difference between N-acetyl-D-glucosamine and N-acetyl glucosamine is that N-acetyl-D-glucosamine is the D isomer of N-acetyl glucosamine, whereas N-acetyl glucosamine is an amide that occurs as a major component in the bacterial cell wall.

Reference:

1. “N-Acetyl-D-Glucosamine.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of Medicine.
2. “N-Acetyl Glucosamine: Health Benefits, Side Effects, Uses, Dose & Precautions.” RxList, 11 June 2021.

Image Courtesy:

1. “N-Acetylglucosamine” By Yikrazuul – Own work (Public Domain) via Commons Wikimedia