D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-

Base Information

• Chemical Name: D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-
• CAS No.: 192126-76-4
• Molecular Formula: C17H30 N2 O12 S
• Molecular Weight: 486.497
• Mol file: 192126-76-4.mol

Synonyms:Mycothiol;U 17

Chemical Property of D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-

Chemical Property:

• PSA: 284.28000
• LogP: -4.77140

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Mycothiol (MSH), also known as D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-, is a low-molecular-weight thiol unique to actinomycetes, including Mycobacterium tuberculosis. It plays a crucial role in bacterial redox homeostasis and detoxification, making it a potential target for antitubercular drug development. Research has focused on synthesizing mycothiol analogues and inhibitors targeting mycothiol-associated enzymes, such as GlcNAc-Ins deacetylase (MshB) and mycothiol-S-conjugate amidase (MCA), to disrupt mycothiol biosynthesis and function, thereby increasing bacterial susceptibility to stress and existing therapeutics.

Technology Process of D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-

There total 12 articles about D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol (1228173-37-2) → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Guidance literature:

1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol; With trifluoroacetic acid;

With pyridine;

DOI:10.3762/bjoc.12.35

Reference yield: 40.0%

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-((R)-2-acetylamino-3-acetylsulfanyl-propionylamino)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester (668481-15-0) → 1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide (669091-43-4) + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Guidance literature:

With magnesium methanolate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/ol0362008

Reference yield:

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (668481-13-8) → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr

2: 1,3-dicyclohexylcarbodiimide

3: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C

4: bis(2-mercaptoethyl)sulfone / H₂O / 120 h / 20 °C

With hydrogenchloride; hydrogen; magnesium methanolate; Bis(2-mercaptoethyl) Sulfone; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; water; ethyl acetate;

DOI:10.1021/ol0362008

upstream raw materials:

1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-((R)-2-acetylamino-3-acetylsulfanyl-propionylamino)-tetrahydro-pyran-2-yloxy]-cyclohexyl ester

(R)-2-acetylamino-3-(acetylthio)propionic acid

Acetic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5-tetraacetoxy-6-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-cyclohexyl ester

Downstream raw materials:

1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside

pyridine-2-thione

Refernces

Synthesis of natural product-inspired inhibitors of Mycobacterium tuberculosis mycothiol-associated enzymes: The first inhibitors of GlcNAc-Ins deacetylase

10.1021/jm070669h

The research focuses on the synthesis and evaluation of a chemical library of inhibitors targeting Mycobacterium tuberculosis mycothiol-associated enzymes, specifically GlcNAc-Ins deacetylase (MshB) and mycothiol-S-conjugate amidase (MCA). The purpose of this study was to develop small molecules that could interfere with mycothiol (MSH) biosynthesis or MSH-assisted detoxification, which could potentially serve as new antitubercular agents. The researchers synthesized a series of inhibitors based on natural product structures known to competitively inhibit MCA. The library of inhibitors was biased to include structural features of these natural products, and molecular docking studies were used to predict their binding modes within the active sites of the target enzymes. The study concluded that the synthesized inhibitors were the first reported to target MshB and supported the potential of natural product-substrate chimeras to act as dual inhibitors for both MshB and MCA. Key chemicals used in the synthesis process included 1-myo-D-inositol (myo-D-Ins), glucosamine (GlcN), N-acetyl-cysteine, and various sulfonyl chlorides, phosphonates, and other organic compounds to construct the desired inhibitor scaffolds and evaluate their biological activity.

Shortcut to mycothiol analogues

10.1021/ol0269796

The research focuses on the synthesis of a simplified thioglycosidic analogue (2) of mycothiol (1), a low molecular weight thiol found in actinomycetes, including Mycobacterium tuberculosis. The purpose of this study is to develop a potential starting point for antitubercular drug design by disrupting the enzymatic pathways of mycothiol biosynthesis and detoxification, which could make M. tuberculosis more vulnerable to drugs and other stress factors. The researchers synthesized analogue 2 and evaluated its specific activity against mycothiol S-conjugate amidase from M. tuberculosis, finding it to be a good substrate with specific activity comparable to mycothiol itself.