86220-45-3

Usage

Uses

Used in Heavy Metal Detoxification:
Cadystin is used as a heavy metal detoxification agent for its ability to bind and sequester heavy metal ions, reducing their toxicity and facilitating their removal from the body.
Used in Environmental Remediation:
Cadystin is used as a bioremediation agent for its potential to mitigate heavy metal pollution in the environment, promoting ecological balance and protecting ecosystems.
Used in Pharmaceutical Industry:
Cadystin is used as a therapeutic agent for its potential applications in treating heavy metal poisoning and related health issues, offering a natural and effective solution for heavy metal detoxification.
Used in Agricultural Industry:
Cadystin is used as a soil amendment for its ability to improve soil health by reducing heavy metal contamination, promoting plant growth, and enhancing crop yields.
Used in Cosmetics Industry:
Cadystin is used as an ingredient in cosmetics for its potential skin protective and detoxifying properties, helping to maintain skin health and prevent damage from environmental pollutants.

InChI:InChI=1/C26H41N7O14S3/c27-11(24(42)43)1-4-17(34)30-15(9-49)22(40)32-13(26(46)47)3-6-19(36)31-16(10-50)23(41)33-12(25(44)45)2-5-18(35)29-14(8-48)21(39)28-7-20(37)38/h11-16,48-50H,1-10,27H2,(H,28,39)(H,29,35)(H,30,34)(H,31,36)(H,32,40)(H,33,41)(H,37,38)(H,42,43)(H,44,45)(H,46,47)/t11-,12-,13-,14-,15-,16-/m0/s1

Synthetic route

Boc-<γ-Glu(OBzl)-Cys(MBzl)>3-Gly-OBzl (131574-49-7) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
With methyl-phenyl-thioether; hydrogen fluoride; 3-methyl-phenol at 0℃; for 1h;	82.8%

H-<γ-Glu-Cys(StBu)>3-Gly-OH (138901-84-5) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
With ammonium acetate; 2-hydroxyethanethiol for 2h; Ambient temperature;	66%

Tr-L-Glu-OBn> (95014-76-9) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
With hydrogen fluoride; ethane-1,2-dithiol; methoxybenzene at 0℃; for 1h;	40%
With hydrogen fluoride

GLUTATHIONE (70-18-8) → N-L-γ-glutamyl-L-cysteine (636-58-8) + H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3) + H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin B <2>) (95014-75-8) + (γ-Glu-Cys)2 (100922-53-0) + (γ-Glu-Cys)3 (118433-03-7)

Conditions	Yield
In water at 37℃; for 4h; transformation by carboxypeptidase Y; pH 9.7;

Nps-<γ-Glu(α-OtBu)-Cys(StBu)>3-Gly-OtBu (138901-82-3) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 2: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 3: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

H-γ-Glu(α-OtBu)-Cys(StBu)-Gly-OtBu (138923-96-3) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions

Yield

Multi-step reaction with 6 steps 1: 82 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 2: 90 percent / methanolic 0.75 N HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 3: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 4: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 5: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 6: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

Nps-Glu(OSu)-OtBu (138901-88-9) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
Multi-step reaction with 9 steps 1: 94 percent / 1N NaOH, NaHCO3 / dioxane; H2O / 12 h / Ambient temperature 2: 84 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 3: 89 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 4: 82 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 5: 90 percent / methanolic 0.75 N HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 6: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 7: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 8: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 9: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme
Multi-step reaction with 7 steps 1: 94 percent / 1N NaOH, NaHCO3 / dioxane; H2O / 12 h / Ambient temperature 2: 82 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 3: 90 percent / methanolic 0.75 N HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 4: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 5: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 6: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 7: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

Nps-γ-Glu(α-OtBu)-Cys(StBu)-OH (138901-78-7) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
Multi-step reaction with 8 steps 1: 84 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 2: 89 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 3: 82 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 4: 90 percent / methanolic 0.75 N HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 5: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 6: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 7: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 8: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: 82 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 2: 90 percent / methanolic 0.75 N HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 3: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 4: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 5: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 6: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 2: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 3: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 4: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

Nps-γ-Glu(α-OtBu)-Cys(StBu)-Gly-OtBu (138923-95-2) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions

Yield

Multi-step reaction with 7 steps 1: 89 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 2: 82 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 3: 90 percent / methanolic 0.75 N HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 4: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 5: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 6: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 7: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

H-<γ-Glu(α-OtBu)-Cys(StBu)>2-Gly-OtBu (138901-80-1) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 2: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 3: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 4: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

Nps-<γ-Glu(α-OtBu)-Cys(StBu)>2-Gly-OtBu (138901-79-8) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions

Yield

Multi-step reaction with 5 steps 1: 90 percent / methanolic 0.75 N HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 2: 79 percent / HOBt, N-ethylmorpholine, DCCI / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 1 h 3: 80 percent / 0.75 N methanolic HCl, 2-methylindole / dioxane / 1 h / Ambient temperature 4: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 5: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

H-<γ-Glu(α-OtBu)-Cys(StBu)>3-Gly-OtBu (138901-83-4) → H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / TFA, ethyl methyl sulfide / 2 h / Ambient temperature 2: 66 percent / 2-mercaptoethanol, 0.1 M ammonium acetate / 2 h / Ambient temperature View Scheme

H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3) → deS-cadystin A (86237-06-1)

Conditions	Yield
Raney-Ni W-2 In water at 50℃; for 12h;

H-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-γ-L-Glu-L-Cys-Gly-OH (cadystin A <1>) (86220-45-3) → C26H38AsN7O14S3

Conditions	Yield
With arsenous acid In water for 16h;

Upstream product

• 70-18-8 GLUTATHIONE 
• 138901-83-4 H-<γ-Glu(α-OtBu)-Cys(StBu)>3-Gly-OtBu 
• 138901-79-8 Nps-<γ-Glu(α-OtBu)-Cys(StBu)>2-Gly-OtBu 
• 138901-80-1 H-<γ-Glu(α-OtBu)-Cys(StBu)>2-Gly-OtBu 
• 138923-95-2 Nps-γ-Glu(α-OtBu)-Cys(StBu)-Gly-OtBu 
• 138901-78-7 Nps-γ-Glu(α-OtBu)-Cys(StBu)-OH 
• 138901-88-9 Nps-Glu(OSu)-OtBu 
• 138923-96-3 H-γ-Glu(α-OtBu)-Cys(StBu)-Gly-OtBu 
• 138901-82-3 Nps-<γ-Glu(α-OtBu)-Cys(StBu)>3-Gly-OtBu 
• 138901-84-5 H-<γ-Glu-Cys(StBu)>3-Gly-OH 
• 95014-76-9 Tr-L-Glu-OBn> 
• 131574-49-7 Boc-<γ-Glu(OBzl)-Cys(MBzl)>3-Gly-OBzl 

Relevant academic research and scientific papers

Conversion of Glutathione into Cadystins and Their Analogs Catalyzed by Carboxypeptidase Y

Cadystins induced in a fission yeast treated with Cd2+ are the higher homologs of glutathione. In the present work, glutathione was incubated with Carboxypeptidase Y at a high substrate concentration. The reaction afforded not only the degraded product, but also cadystins and their analogs. A possible transformation pathway for glutathione by this enzyme is proposed.

Solution Synthesis of Phytochelatins, Isopeptides from the Plant Kingdom

Phytochelatins which are linear peptide polymers of the γ-glutamylcysteine portion of glutathione with the general formula H-n-Gly-OH (n=2-11) are the main components for the detoxification of heavy metals in the plant kingdom.So far these peptides have been mostly obtained by isolation from cell suspension cultures.We have now prepared some of these (n=2-4) by the classical solution synthesis under mild conditions.For the protection of amino, carboxyl and thiol functions Nps, tBu and StBu protecting groups have been employed, respectively.The characterization of the peptide intermediates and final products has been achieved by mass spectrometry, 13C-NMR spectroscopy and amino acid analysis. Key Words: Phytochelatins / Isopeptide bond / Glutathione

Synthesis of Metallothionein-like Peptides Cadystin A and B Occurring in a Fission Yeast, and Their Isomers

The unit peptides, cadystin A and B, in the cadmium-containing peptides occurring in a fission yeast were synthesized for conformation of the structure.Four possible stereoisomers of the previously proposed structure for cadystin were also synthesized.

CADYSTIN A AND B, MAJOR UNIT PEPTIDES COMPRISING CADMIUM BINDING PEPTIDES INDUCED IN A FISSION YEAST-----SEPARATION, REVISION OF STRUCTURES AND SYNTHESIS

The unit peptide, cadystin, of the cadmium-binding peptides occuring in a fission yeast was further separated into two major components, cadystin A and B, structures of which were determined to be 1 and 2, respectively, and confirmed by synthesis.The structure previously reported for cadystin was thus revised.