86220-45-3

Basic information

• Product Name: cadystin
• Synonyms: cadystin;(γ-Glu-Cys)3Gly;(γGlu-Cys)3Gly;Cadystin A;L-γGlu-L-Cys-L-γGlu-L-Cys-L-γGlu-L-Cys-Gly-OH;γGlu-Cys-γGlu-Cys-γGlu-Cys-Gly-OH;γGlu-L-Cys-γGlu-L-Cys-γGlu-L-Cys-Gly-OH;Cadystin protein, S pombe
• CAS NO: 86220-45-3
• Molecular Formula: C₂₆H₄₁N₇O₁₄S₃
• Molecular Weight: 771.83724
• Mol File: 86220-45-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 1375.8°C at 760 mmHg
• Flash Point: 785.8°C
• Appearance: /
• Density: 1.484g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.598
• CAS DataBase Reference: cadystin(CAS DataBase Reference)
• NIST Chemistry Reference: cadystin(86220-45-3)
• EPA Substance Registry System: cadystin(86220-45-3)

Safety Data

• Hazardous Substances Data: 86220-45-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A phytochelatin that is a heptapeptide consisting of 3 units of gamma-Glu-Cys, with a glycyl unit at the C-terminus.

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

• 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 
• 70-18-8 GLUTATHIONE 
• 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 articles and documents

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.

Amino acids and peptides. XXVII. Synthesis of phytochelatin-related peptides and examination of their heavy metal-binding properties

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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.