192126-76-4

Usage

Uses

Used in Pharmaceutical Industry:
D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]is used as a pharmaceutical agent for its potential therapeutic effects. D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-'s unique structure allows it to interact with various biological systems, making it a candidate for the development of new drugs targeting specific health conditions.
Used in Biochemical Research:
In the field of biochemistry, D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]is utilized for studying the roles of inositol, glucosamine, and thiol groups in cellular processes. Its presence in biochemical assays can provide insights into the mechanisms of cell membrane function, chitin synthesis, and antioxidant activity.
Used in Nutraceutical Development:
D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]is used as a nutraceutical ingredient for its potential health benefits. D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-'s antioxidant properties and involvement in cell membrane integrity may contribute to overall health and wellness, making it a valuable addition to dietary supplements and functional foods.
Used in Cosmetics Industry:
In the cosmetics industry, D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]is used as an active ingredient for its skin health-promoting properties. D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]-'s role in cell membrane function and its antioxidant capabilities can contribute to the development of skincare products that promote skin hydration, elasticity, and protection against environmental stressors.

Synthetic route

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)

Conditions	Yield
Stage #1: 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol With trifluoroacetic acid Stage #2: With pyridine	100%

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)

Conditions	Yield
With magnesium methanolate In methanol at 20℃; for 2h;	A 29% B 40%

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)

Conditions	Yield
With Bis(2-mercaptoethyl) Sulfone In water at 20℃; for 120h;
With ethylenediaminetetraacetic acid; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; NADPH-dependent mycothiol disulfide reductase In water; dimethyl sulfoxide at 30℃; pH=7.5; Enzyme kinetics;

(R)-2-acetylamino-3-(acetylthio)propionic acid (18725-37-6) → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,3-dicyclohexylcarbodiimide 2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C 3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 1,3-dicyclohexylcarbodiimide 2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C 2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C 3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C 2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C View Scheme

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)

Conditions	Yield
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 View Scheme
Multi-step reaction with 3 steps 1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr 2: 1,3-dicyclohexylcarbodiimide 3: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr 2: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C 3: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C 4: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 81 percent / hydrogen; HCl / palladium on carbon / ethyl acetate / 6 h / 20 °C / 760.21 Torr 2: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C 3: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C View Scheme

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-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C 2: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C View Scheme

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-amino-tetrahydro-pyran-2-yloxy)-cyclohexyl ester; hydrochloride → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,3-dicyclohexylcarbodiimide 2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C 3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 1,3-dicyclohexylcarbodiimide 2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C 2: 29 percent / Mg(OMe)2 / methanol / 2 h / 20 °C 3: bis(2-mercaptoethyl)sulfone / H2O / 120 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 25 percent / 2,4,6-collidine; 1-hydroxy-7-azabenzotriazole; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF6 / dimethylformamide / 0 - 20 °C 2: 40 percent / Mg(OMe)2 / methanol / 2 h / 20 °C View Scheme

C2HF3O2*C17H30N2O12S → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
With pyridine for 0.5h;	3.3 mg

1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol hydrochloride (1228173-30-5) → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 4 - 20 °C / Inert atmosphere 2: trifluoroacetic acid / 0.33 h / 4 °C 3: pyridine / 0.5 h / 20 °C View Scheme

C17H30N2O12S → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
With pyridine at 20℃; for 0.5h;	4.4 mg

1-O-[2-azido-3-O-(4-bromobenzyl)-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol (1334379-58-6) → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride; hydrogen; palladium(II) hydroxide / methanol; water / 72 h 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 4 - 20 °C / Inert atmosphere 3: trifluoroacetic acid / 0.33 h / 4 °C 4: pyridine / 0.5 h / 20 °C View Scheme

N-(tert-butoxycarbonyl)-S-acetyl-L-cysteine (21948-02-7) → 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 4 - 20 °C / Inert atmosphere 2: trifluoroacetic acid / 0.33 h / 4 °C 3: pyridine / 0.5 h / 20 °C View Scheme

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4) → mycothione

Conditions	Yield
With iodine In methanol for 0.25h;	100%

monobromobimane (71418-44-5) + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4) → 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside (158761-05-8)

Conditions	Yield
With sodium hydrogencarbonate In water; acetonitrile at 20℃; for 2h;	78%
With tris hydrochloride pH=8.0;

C26H46N5O8S(1+) + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4) → C9H16N3O2S(1+) + C34H60N4O18S

Conditions	Yield
Microbiological reaction;

C55H79ClN9O15PolS2 + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol (192126-76-4) → pyridine-2-thione (2637-34-5) + C67H104ClN10O27PolS2

Conditions	Yield
In aq. buffer for 3h; chemoselective reaction;

Upstream product

• 18725-37-6 (R)-2-acetylamino-3-(acetylthio)propionic acid 
• 1228173-30-5 1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol hydrochloride 
• 1334379-58-6 1-O-[2-azido-3-O-(4-bromobenzyl)-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol 
• 21948-02-7 N-(tert-butoxycarbonyl)-S-acetyl-L-cysteine 
• 1228173-37-2 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol 
• 668481-15-0 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 
• 668481-13-8 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 
• 669091-43-4 1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide 

Downstream Products

• 158761-05-8 1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside 
• 2637-34-5 pyridine-2-thione 

Relevant academic research and scientific papers

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

Mycothiol is found in Gram-positive bacteria, where it helps in maintaining a reducing intracellular environment and it plays an important role in protecting the cell from toxic chemicals. The inhibition of the mycothiol biosynthesis is considered as a treatment for tuberculosis. Mycothiol contains an α-aminoglycoside, which is difficult to prepare stereoselectively by a conventional glycosylation reaction. In this study, mycothiol was synthesized by an anomerization reaction from an easily prepared β-aminoglycoside through endocyclic cleavage.

Desymmetrization of 2,4,5,6-tetra-o-benzyl-d-myo-inositol for the synthesis of mycothiol

An efficient chemical synthesis of mycothiol involving the regioselective ketopinyl desymmetrization of 2,4,5,6-tetrabenzylated d-myo-inositol as the key step is described. Together with a highly α-stereoselective d-glucosaminylation, the whole procedure was accomplished in eight steps with an overall yield of 40%.

Intramolecular α-glucosaminidation: Synthesis of mycothiol

A protected cyclitol aglycon was tethered to an (N-arylsulfonyl)glucosamine donor by a methylene linker; the exclusively α-selective intramolecular glycosyation reaction was then initiated by electrophilic activation of the thioglycoside donor portion. Further transformations of the glycosylation product to give the M. tuberculosis detoxifier mycothiol and its oxidized congener, the disulfide mycothione, are detailed.

Mycothiol disulfide reductase: Solid phase synthesis and evaluation of alternative substrate analogues

A solid phase synthesis of des-myo-inositol mycothiol disulfide and its alpha-configured methyl- and benzyl-glycoside derivatives has been developed. Kinetic characterisation of these compounds has demonstrated their viability as alternative substrates for use in mycothiol disulfide reductase enzyme assays. This journal is The Royal Society of Chemistry.

First Total Synthesis of Mycothiol and Mycothiol Disulfide

(Matrix presented) The first total synthesis of mycothiol and mycothiol disulfide was achieved by linking D-2,3,4,5,6-penta-O-acetyl-myo-inositol, O-(3,4,6-tri-O-acetyl)-2-azido-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate, and N,S-diacetyl-L-cysteine and deprotecting peracetylated mycothiol. The first full spectral characterization is reported for underivatized mycothiol. The structure of mycothiol was confirmed by spectral analysis of the known bimane derivative.