921-01-7

Basic information

• Product Name: D-Cysteine
• Synonyms: D-Cysteine >=99% (RT);D-Cysteine, 98%, 98%;H-D-CYS-OH;D-CYS-OH;D-CYSTEINE;BETA-MERCAPTOALANINE;(S)-2-AMINO-3-MERCAPTOPROPIONIC ACID;RARECHEM AB PP 1441
• CAS NO: 921-01-7
• Molecular Formula: C₃H₇NO₂S
• Molecular Weight: 121.16
• EINECS: 213-062-0
• Product Categories: Amino Acids
• Mol File: 921-01-7.mol
• Article Data: 155

Chemical Properties

• Melting Point: ~230 °C
• Boiling Point: 293.9 °C at 760 mmHg
• Flash Point: 131.5 °C
• Appearance: White/Crystalline Powder
• Density: 1.335 g/cm³
• Vapor Pressure: 0.000411mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: −20°C
• Solubility: Aqueous Acid (Slightly), Water (Slightly)
• PKA: 2.07±0.10(Predicted)
• Water Solubility: Soluble in water (partly).
• Sensitive: Air Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 1721407
• CAS DataBase Reference: D-Cysteine(CAS DataBase Reference)
• NIST Chemistry Reference: D-Cysteine(921-01-7)
• EPA Substance Registry System: D-Cysteine(921-01-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-22
• Safety Statements: 26-36-37/39-22
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 921-01-7(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

D-Cysteine has been used in the functionalization of QDs for applications in photocatalysis. It can also be used in the synthesis of: cysteine-based chiral carbon dots (CDs) D-luciferin and aminoluciferin analogs

Definition

ChEBI: An optically active form of cysteine having D-configuration.

InChI:InChI=1/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1

Synthetic route

L-thiaproline (444-27-9, 19291-02-2, 34592-47-7, 45521-09-3) → D-cysteine (921-01-7)

Conditions	Yield
With hydroxylamine hydrochloride	83%
With hydroxylamine hydrochloride In methanol reflux, 120 min, ice bath, 60 min;	82%

(4S-)-2-(D-gluco-1,2,3,4,5-Pentahydroxypentyl)-4-thiazolidincarbonsaeure (17087-37-5, 17087-38-6, 17205-71-9, 57918-01-1, 85504-88-7, 85504-89-8, 88271-26-5, 88271-27-6, 88271-28-7, 88271-29-8, 88271-30-1, 110270-21-8, 110270-23-0, 110311-43-8, 124650-44-8, 124650-45-9, 124650-46-0, 124650-49-3, 124650-50-6, 124650-51-7, 132338-92-2, 149885-33-6) → D-cysteine (921-01-7)

Conditions	Yield
With hydroxylamine hydrochloride In methanol; water for 4h; Heating;	79%

(4S)-2-(D-manno-1,2,3,4,5-Pentahydroxypentyl)-4-thiazolidincarbonsaeure (17087-37-5, 17087-38-6, 17205-71-9, 57918-01-1, 85504-88-7, 85504-89-8, 88271-26-5, 88271-27-6, 88271-28-7, 88271-29-8, 88271-30-1, 110270-21-8, 110270-23-0, 110311-43-8, 124650-44-8, 124650-45-9, 124650-46-0, 124650-49-3, 124650-50-6, 124650-51-7, 132338-92-2, 149885-33-6) → D-cysteine (921-01-7)

Conditions	Yield
With hydrazine hydrate In methanol for 0.75h; Heating;	75%

(2S,4S)-2-(D-galacto-1,2,3,4,5-Pentahydroxypentyl)-4-thiazolidincarbonsaeure (88271-26-5) → D-cysteine (921-01-7)

Conditions	Yield
With hydroxylamine hydrochloride In methanol for 2h; Heating;	73%

(4S)-2-(L-arabino-1,2,3,4-Tetrahydroxybutyl)-4-thiazolidincarbonsaeure (17087-36-4, 59246-17-2, 88271-31-2, 110270-13-8, 110270-14-9, 110270-15-0, 110270-16-1, 110270-17-2, 110270-18-3, 110270-19-4, 110270-20-7, 115184-30-0, 124650-47-1, 124650-48-2) → D-cysteine (921-01-7)

Conditions	Yield
With hydroxylamine hydrochloride In methanol; water for 3.5h; Heating;	60%

rac-cysteine (921-01-7, 3374-22-9, 4371-52-2, 40143-64-4, 40143-66-6, 40143-69-9, 52-90-4) → D-cysteine (921-01-7)

Conditions	Yield
beim selektiven Abbau durch Escherichia coli;

S,S-cystine (349-46-2) → D-cysteine (921-01-7)

Conditions	Yield
With hydrogenchloride; tin

(D)-2-Amino-3-(benzylthio)propanoic acid (3054-01-1, 5680-65-9, 16597-46-9, 23032-53-3) → D-cysteine (921-01-7)

Conditions	Yield
With ammonia; sodium

(2R,2'R)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid (2998-83-6) → D-cysteine (921-01-7)

Conditions	Yield
Spaltung durch Leber-Extrakt;

L-Cysteine (52-90-4) → D-cysteine (921-01-7)

Conditions	Yield
With water; acetone Product distribution; 1.) acetic acid, reflux, 2.5 h; 2.) methanol, room temp, 30 min;

3-chloro-DL-alanine (3981-36-0) → D-cysteine (921-01-7)

Conditions	Yield
With sodium hydrogensulfide; potassium phosphate buffer; acetone at 30℃; for 2h; 3-chloro-D-alanine-lyase; Yield given;

(S)-3-chloroalanine (2731-73-9, 3981-36-0, 13215-35-5, 39217-38-4) → D-cysteine (921-01-7)

Conditions	Yield
With dinitrogen sulphide; pyridoxal 5'-phosphate; sodium dodecyl-sulfate at 30℃; for 3.5h; Pseudomonas fluorescens CR 19-1, 0.1 M phosphate buffer, pH 8.5;
With sodium hydrogensulfide; potassium phosphate buffer; pyridoxal 5'-phosphate In acetone at 30℃; for 2h; Pseudomonas putida CR 1-1 cells; Yield given;

4-ethylbenzenesulfonic acid D-cysteine salt → D-cysteine (921-01-7)

Conditions	Yield
With triethylamine In methanol for 0.5h;

rac-cysteine (921-01-7, 3374-22-9, 4371-52-2, 40143-64-4, 40143-66-6, 40143-69-9, 52-90-4) → D-cysteine (921-01-7) + L-Cysteine (52-90-4)

Conditions	Yield
With teicoplanin In methanol; water Product distribution; Further Variations:; Reagents; pH-values; Solvents;
Resolution of racemate; enantioselective reaction;	A n/a B n/a
Resolution of racemate; enantioselective reaction;	A n/a B n/a
With R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 coated C18 silica gel column at 25℃; pH=2; Resolution of racemate;
With capillary electrochromatography open-tubular column coated with 1-allylimidazolium-β-cyclodextrin In aq. acetate buffer at 20℃; pH=8; pH-value; Resolution of racemate;

hydrgensulfide(1-) + L-cystine (6020-39-9) → D-cysteine (921-01-7) + disulfide

Conditions	Yield
In further solvent(s) Kinetics; in pH 10.0 borate buffer; detected with UV-vis sectroscopy and ion-exchange chromatography;

hapalocyclamide (1359827-55-6) → L-alanin (56-41-7) + D-Alanine (338-69-2) + D-cysteine (921-01-7) + Phenylalanine (150-30-1)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 19h;

hapalocyclamide (1359827-55-6) → D-Alanine (338-69-2) + D-cysteine (921-01-7) + L-phenylalanine (63-91-2) + D-(R)-phenylalanine (673-06-3)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 1h;

Z-Ile-Glu(OMe)-Thr-Asp(OMe)-D-Cys → D-cysteine (921-01-7)

Conditions	Yield
With caspase 8 for 1h;

D-cysteine (921-01-7) + 2,4-Di-tert-butoxy-pyrimidine-5-carbaldehyde (172949-72-3) → (2S,4S)-2-(2,4-Di-tert-butoxy-pyrimidin-5-yl)-thiazolidine-4-carboxylic acid (1025823-01-1)

Conditions	Yield
In ethanol; water	100%

D-cysteine (921-01-7) + propyl bromide (106-94-5) → S-propyl-D-cysteine (85955-34-6)

Conditions	Yield
With ammonia; sodium	98%

D-cysteine (921-01-7) + allyl alcohol (107-18-6) → Fudosteine

Conditions	Yield
With potassium sulfate In water at 30℃;	98%

D-cysteine (921-01-7) + tert-butyl 4-iodobutanoate (6182-78-1) → 4-((2S)-amino-2-carboxy-ethylsulfanyl)-butyric acid tert-butyl ester

Conditions	Yield
Stage #1: D-cysteine With sodium hydroxide; water In methanol at 0℃; Stage #2: tert-butyl 4-iodobutanoate In methanol for 0.0833333h; Stage #3: With hydrogenchloride; water In methanol pH=~ 8;	97%

D-cysteine (921-01-7) + 2-cyano-6-hydroxybenzothiazole (939-69-5) → D-luciferin (2591-17-5)

Conditions	Yield
In water at 20℃;	95%
With ammonia; sodium In methanol; water	94%
Stage #1: D-cysteine; 2-cyano-6-hydroxybenzothiazole In aq. buffer for 1h; Stage #2: With ATP; magnesium chloride; zinc(II) chloride; luciferase In aq. buffer	27%

methanol (67-56-1) + D-cysteine (921-01-7) → D-cysteine methyl ester hydrochloride (5714-80-7, 18598-63-5, 70361-61-4)

Conditions	Yield
With acetyl chloride at 0℃; for 2h; Reflux;	94%
With hydrogenchloride for 12h;
With hydrogenchloride at 100℃; for 0.5h;

ethyleneimine (151-56-4) + D-cysteine (921-01-7) → 2-amino-3-<(2-aminoethyl)thio>-propanoic acid (53526-71-9)

Conditions	Yield
With phosphate buffer at 0℃; pH 8.0;	92%

D-cysteine (921-01-7) + mono-4-methoxytrityl chloride (14470-28-1) → C23H23NO3S (926935-33-3)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	92%

6-(methylamino)benzo[d]-thiazole-2-carbonitrile (934270-86-7) + D-cysteine (921-01-7) → D-(-)-2-(6'-methylamino-2'-benzothiazolyl)-Δ2-thiazoline-4-carboxylic acid

Conditions	Yield
In methanol for 1h; pH=8; aq. sodium phosphate buffer; Inert atmosphere;	91%

D-cysteine (921-01-7) + 2-Hydroxy-3-methoxybenzonitrile (6812-16-4) → (S)-2-(2-Hydroxy-3-methoxy-phenyl)-4,5-dihydro-thiazole-4-carboxylic acid

Conditions	Yield
With phosphate buffer In methanol at 70℃; for 17h;	90%

methanol (67-56-1) + D-cysteine (921-01-7) → (S)-(+)-Cysteinmethylester

Conditions	Yield
Stage #1: methanol With acetyl chloride at 0℃; for 0.0833333h; Stage #2: D-cysteine for 6h; Reflux;	90%

D-cysteine (921-01-7) + di-tert-butyl dicarbonate (24424-99-5) → N,N’-di-Boc-L-cystine (126686-73-5)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water for 24h; pH=10;	89%

D-cysteine (921-01-7) + 6-((4-(dimethylamino)phenyl)amino)benzo[d]thiazole-2-carbonitrile → (S)-2-(6-((4-(dimethylamino)phenyl)amino)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; aq. phosphate buffer for 1h; pH=8; Inert atmosphere;	88%

ethanol (64-17-5) + D-cysteine (921-01-7) → D-cysteine ethyl ester hydrochloride (75521-14-1)

Conditions	Yield
Stage #1: ethanol With thionyl chloride at -5 - 20℃; for 1.5h; Stage #2: D-cysteine at 50℃; for 4h;	87.5%

D-cysteine (921-01-7) + 2,4-Dimethoxybenzaldehyde (613-45-6) → C12H15NO4S

Conditions	Yield
In ethanol at 20℃; for 48h;	87%

D-cysteine (921-01-7) + N-(2-cyanobenzo[d]thiazol-6-yl)ethanesulfonamide → (S)-2-(6-(ethylsulfonamido)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; aq. phosphate buffer for 1h; pH=8;	86%

D-cysteine (921-01-7) + N-(2-cyanobenzo[d]thiazol-6-yl)methanesulfonamide → (S)-2-(6-(methylsulfonamido)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In aq. phosphate buffer; acetonitrile for 1h; pH=8;	86%

D-cysteine (921-01-7) + benzyl chloroformate (501-53-1) + methyl iodide (74-88-4) → N-(benzyloxycarbonyl)-S-methyl-D-cysteine (95406-98-7)

Conditions	Yield
Stage #1: D-cysteine; methyl iodide With sodium In methanol Stage #2: benzyl chloroformate With sodium hydroxide	85%

diethyl sulfate (64-67-5) + D-cysteine (921-01-7) → (S)-2-amino-3-(ethylthio)propanoic acid

Conditions	Yield
With barium(II) hydroxide at 20℃; for 3h;	85%

D-cysteine (921-01-7) + (4-hydroxyphenyl)methanol (623-05-2) → D-[S-(4'-hydroxybenzyl)]cysteine

Conditions	Yield
With hydrogenchloride In water at 20℃; for 0.333333h; pH=2;	84.7%

D-cysteine (921-01-7) + 6-((4-hydroxyphenyl)amino)benzo[d]thiazole-2-carbonitrile → (S)-2-(6-((4-hydroxyphenyl)amino)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; aq. phosphate buffer for 1h; pH=8; Inert atmosphere;	84%

D-cysteine (921-01-7) + 6-(2-oxooxazolidin-3-yl)benzo[d]thiazole-2-carbonitrile → (S)-2-(6-(2-oxooxazolidin-3-yl)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; aq. phosphate buffer for 1h; pH=8; Inert atmosphere;	84%

D-cysteine (921-01-7) + 5-methoxythiazolo[5,4-b]pyridine-2-carbonitrile (1417816-65-9) → (S)-2-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
With potassium carbonate In water; N,N-dimethyl-formamide; acetonitrile for 0.166667h;	83%

D-cysteine (921-01-7) + 6-fluorobenzo[d]thiazole-2-carbonitrile (169776-04-9) → (S)-2-(6-fluorobenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; aq. phosphate buffer for 1h; pH=8; Inert atmosphere;	81%

D-cysteine (921-01-7) + N-(2-cyanobenzo[d]thiazol-6-yl)cyclopentanesulfonamide → (S)-2-(6-(cyclopentanesulfonamido)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; aq. phosphate buffer for 1h; pH=8;	80%

D-cysteine (921-01-7) + 2-cyanobenzo[d]thiazol-6-yl 4-oxopentanoate → (S)-2-(6-((4-oxopentanoyl)oxy)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; dichloromethane; water at 0 - 25℃; for 0.5h; Inert atmosphere;	79.7%

D-cysteine (921-01-7) + N-(2-cyanobenzo[d]thiazol-6-yl)propane-2-sulfonamide → (S)-2-(6-(1-methylethylsulfonamido)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Conditions	Yield
In methanol; aq. phosphate buffer for 1h; pH=8;	79%

1-(3',4'-dihydroxyphenyl)decan-3-one + D-cysteine (921-01-7) → 3’-S-cysteinyl-1-(3,4-dihydroxyphenyl)decan-3-one

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In methanol; aq. phosphate buffer at -78 - 20℃; for 1.5h;	78%

Upstream product

• 56-89-3 cysteine disulfide 
• 56-89-3 L-cystine 
• 143-33-9 sodium cyanide 
• 19538-81-9 N,S-diacetyl-cysteine 
• 91641-78-0 N-benzoyl-cysteine ethyl ester 
• 5680-65-9 2-amino-3-(benzylthio)propionic acid 
• 52-90-4 L-Cysteine 
• 7732-18-5 water 
• 10034-85-2 hydrogen iodide 
• 922-56-5 meso-lanthionine 
• 600-05-5 2,3-dibromopropionic acid 
• 498-59-9 S,S'-methylenebis(cysteine) 
• 7664-93-9 sulfuric acid 
• 7218-04-4 N-Acetylcysteine 

Downstream Products

• 109819-52-5 N,S-bis-[(2,4,5-trichloro-phenoxy)-acetyl]-cysteine 
• 75-07-0 acetaldehyde 
• 56-89-3 cysteine disulfide 
• 6020-39-9 L-cystine 
• 923-32-0 DL-cystine 
• 56-89-3 L-cystine 
• 107-36-8 2-hydroxyethanesulfonic acid 
• 349-46-2 S,S-cystine 
• 16708-09-1 2-methyl-thiazolidine-2,4-dicarboxylic acid 
• 63892-69-3 Thioacetic acid S-(2-acetylamino-3-oxo-butyl) ester 
• 97800-36-7 C₁₅H₁₄N₄O₄S₂ 
• 15139-21-6 5-thio-2-nitrobenzoic acid 
• 89461-64-3 (7E,9E,11Z,14Z)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester 

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