CAS No.192126-76-4,D-myo-Inositol,1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-a-D-glucopyranosyl]- Suppliers

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Mycothiol Application:chemical research

Mycothiol

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Synthetic route

: 1228173-37-2
1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol

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

Conditions

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%

: 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

A: 669091-43-4
1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide

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

Conditions

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

: 669091-43-4
1-D-myo-inosityl-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-α-D-glucopyranoside disulfide

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

Conditions

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;

: 18725-37-6
(R)-2-acetylamino-3-(acetylthio)propionic acid

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

Conditions

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

: 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

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

Conditions

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

: 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

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

Conditions

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

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

Conditions

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

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

Conditions

Conditions	Yield
With pyridine for 0.5h;	3.3 mg

: 1228173-30-5
1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol hydrochloride

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

Conditions

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

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

Conditions

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

: 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

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

Conditions

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

: 21948-02-7
N-(tert-butoxycarbonyl)-S-acetyl-L-cysteine

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

Conditions

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

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

: mycothione

Conditions

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

: 71418-44-5
monobromobimane

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

: 158761-05-8
1-D-myo-inosityl-2-deoxy-2-(N-acetamido-L-cysteinamido)-α-D-glucopyranoside

Conditions

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

: C26H46N5O8S(1+)

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

A: C9H16N3O2S(1+)

B: C34H60N4O18S

Conditions

Conditions	Yield
Microbiological reaction;

...Expand

: C55H79ClN9O15PolS2

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

A: 2637-34-5
pyridine-2-thione

B: C67H104ClN10O27PolS2

Conditions

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

...Expand

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