6027-15-2

Basic information

• Product Name: D-HOMOCYSTINE
• Synonyms: D-HOMOCYSTINE;D-4,4'-DITHIOBIS[2-AMINOBUTANOIC ACID];(H-D-HOCYS-OH)2;(R,R)-4,4-DITHIOBIS(2-AMINOBUTANOIC ACID);(H-D-Hcys-OH) 2;Butanoic acid, 4,4'-dithiobis[2-aMino-, (2R,2'R)-;(2R,2'R)-4,4'-Disulfanediylbis(2-aminobutanoic acid)
• CAS NO: 6027-15-2
• Molecular Formula: C₈H₁₆N₂O₄S₂
• Molecular Weight: 268.35
• Mol File: 6027-15-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 507.58 °C at 760 mmHg
• Flash Point: 260.775 °C
• Appearance: /
• Density: 1.444 g/cm³
• Storage Temp.: Store at 0-5°C
• Solubility: Aqueous Acid (Slightly), Methanol (Slightly)
• PKA: 1.90±0.10(Predicted)
• CAS DataBase Reference: D-HOMOCYSTINE(CAS DataBase Reference)
• NIST Chemistry Reference: D-HOMOCYSTINE(6027-15-2)
• EPA Substance Registry System: D-HOMOCYSTINE(6027-15-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6027-15-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 6027-15-2 differently. You can refer to the following data:
1. D-Homocysteine is the stereoisomer of L-Homocystine, increased levels lead to hyperhomocysteinemia; a cardiovascular risk factor in prediction of coronary heart disease as well as being associated wit h congenital birth defects, pregnancy complications and cancer.
2. D-Homocysteine is the stereoisomer of L-Homocystine, increased levels lead to hyperhomocysteinemia; a cardiovascular risk factor in prediction of coronary heart disease as well as being associated with congenital birth defects, pregnancy complications and cancer.

Synthetic route

D-homocysteine (454-28-4, 454-29-5, 6027-13-0, 6027-14-1) → D-homocystine (6027-15-2)

Conditions	Yield
With dihydrogen peroxide for 8h;	95.5%
With dopamine In aq. buffer pH=5; Kinetics; Reagent/catalyst; Electrochemical reaction;

(R)-1,3-thiazane-4-carboxylic acid (147331-82-6) → D-homocystine (6027-15-2)

Conditions	Yield
With dihydrogen peroxide	49%

S-benzyl-D-homocysteine (13073-47-7) → D-homocystine (6027-15-2)

Conditions	Yield
With ammonia; sodium Einwirkung von Luft auf das gebildete Natriumsalz des D-Homocysteins in wss.Loesung unter Zusatz von FeCl3;

L-homoserine (672-15-1) → D-homocystine (6027-15-2)

Conditions	Yield
With sodium hydrogensulfide In ethanol

D-methionine (348-67-4) → D-homocystine (6027-15-2)

Conditions	Yield
Stage #1: D-methionine With ammonia; lithium at -78℃; for 1.33333h; Birch Reduction; Stage #2: With hydrogenchloride In water pH=4-5; Cooling; Stage #3: With dihydrogen peroxide In water at 0 - 20℃; for 18h;

D-homocystine (6027-15-2) + di-tert-butyl dicarbonate (24424-99-5) → N,N'-di(tert-butoxycarbonyl)homocystine (113132-85-7)

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 20℃;	100%

D-homocystine (6027-15-2) → D-Homocysteic acid

Conditions	Yield
With bromine In water

D-homocystine (6027-15-2) + carbocyclic 5'-chloro-5'-deoxyadenosine (57816-79-2) → D-C-AdoHcy (94842-39-4)

Conditions	Yield
With ammonia; sodium 1.) -78 deg C; Yield given. Multistep reaction;

D-homocystine (6027-15-2) → D-homocysteine (454-28-4, 454-29-5, 6027-13-0, 6027-14-1)

Conditions	Yield
With diothiothreitol at 30℃; for 5h;

D-homocystine (6027-15-2) + isopropyl bromide (75-26-3) → (R)-2-Amino-4-isopropylsulfanyl-butyric acid (37841-10-4)

Conditions	Yield
With ammonia; sodium
Stage #1: D-homocystine With ammonia; sodium Stage #2: isopropyl bromide

D-homocystine (6027-15-2) → D-Homocysteine monosodium salt (88945-99-7)

Conditions	Yield
With ammonia; sodium

D-homocystine (6027-15-2) → di(tert-butyl) N,N'-bis(tert-butoxycarbonyl)homocystinate (180915-09-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / 1,4-dioxane; water / 20 °C 2: dichloromethane / 20 °C View Scheme

D-homocystine (6027-15-2) → C4H7NO2S(2-)

Conditions	Yield
With ammonia; sodium for 0.333333h;

methanol (67-56-1) + D-homocystine (6027-15-2) + di-tert-butyl dicarbonate (24424-99-5) → dimethyl 4,4'-disulfanediyl(2R,2'R)-bis(2-((tert-butoxycarbonyl)amino)butanoate)

Conditions	Yield
Stage #1: methanol; D-homocystine With thionyl chloride at 0 - 75℃; for 27h; Stage #2: di-tert-butyl dicarbonate With sodium carbonate In dichloromethane; water at 20℃; for 18h;

Upstream product

• 147331-82-6 (R)-1,3-thiazane-4-carboxylic acid 
• 139427-42-2 S-nitroso-L-homocysteine 
• 63-68-3 L-methionine 
• 6027-13-0 L-homocysteine 
• 75027-08-6 (S)-2-Amino-4-[(R)-2-((S)-3-amino-3-carboxy-propyldisulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid 
• 7689-60-3 S-benzyl-L-homocysteine 
• 348-67-4 D-methionine 
• 454-28-4 D-homocysteine 
• 672-15-1 L-homoserine 
• 13073-47-7 S-benzyl-D-homocysteine 

Downstream Products

• 1001-13-4 D-Homocysteic acid 
• 6367-73-3 S-<2-(Toluol-4-sulfonylamido)-aethyl>-L-homocystein 
• 14857-77-3 L-homocysteic acid 
• 454-28-4 D-homocysteine 
• 6027-13-0 L-homocysteine 
• 75027-08-6 (S)-2-Amino-4-[(R)-2-((S)-3-amino-3-carboxy-propyldisulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid 
• 73488-65-0 (methyl-¹³C,D₃)-L-methionine 
• 1492-24-6 L-2-aminobutyric acid 
• 181370-86-5 Fmoc-L-homocystine 
• 147857-42-9 L-Homocystine dimethyl ester dihydrochloride 
• 255387-50-9 bis-N-trifluoroacetyl homocysteine 
• 840476-05-3 (S)-2-Amino-4-[(3aS,4S,6R,6aR)-6-(6-benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethylsulfanyl]-butyric acid 
• 40950-52-5 AdoHcy 
• 840476-08-6 (S)-2-Amino-4-[(2S,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethylsulfanyl]-butyric acid 

Relevant articles and documents

Electrocatalytic oxidation and determination of homocysteine at nanotubes-modified carbon paste electrode using dopamine as a mediator

A carbon paste electrode modified with multiwall carbon nanotubes (MWCNTPE) was prepared to study the electrocatalytic activity of dopamine (DP) in the presence of homocysteine (HCy) and it was used for the determination of HCy. The diffusion coefficient of HCy (D = 6.79×10-6cm 2s-1),and the kinetic parameters of its oxidation, such as electron transfer coefficient (a = 0.46), and rate constant (kh= 7.44×102dm3mol-1s-1)were also determined using electrochemical approaches. Under the optimum pH of 5.0, the peak current of oxidation of HCy at MWCNTPE in the presence of DP occurred at a potential of about 530 mV and the results showed that the oxidation peak current of HCy at the modified carbon nanotubes electrode was higher than on the unmodified electrode. The peak current of differential pulse voltammograms of HCy solutions increased linearly in the range 3.0-600 μM HCy with a detection limit of 2.08 μM HCy. This method was also examined for determination of HCy in physiological serum and urine samples.

METHOD OF PRODUCING S-ICA RIBOSYLHOMOCYSTEINE

PROBLEM TO BE SOLVED: To provide novel techniques regarding a method of producing S-ICA ribosylhomocysteine. SOLUTION: A method of producing a compound represented by formula (1) or a salt thereof comprises reacting a compound represented by formula (2) with a compound represented by formula (3) to generate a compound represented by formula (4), and subjecting the obtained compound represented by formula (4) to a treatment of removing a protecting group. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Colorimetric and fluorometric determination of homocysteine and cysteine

Colorimetric and fluorometric methods are disclosed for the rapid, accurate, selective, and inexpensive detection of homocysteine, or of homocysteine and cysteine, or of cysteine. The methods may be employed with materials that are readily available commercially. The novel methods are selective for homocysteine, for cysteine, or for total homocysteine and cysteine, and do not cross-react substantially with chemically-related species such as glutathione. The homocysteine-selective method does not have substantial cross-reactivity to the very closely related species cysteine. The cysteine-selective method does not have substantial cross-reactivity to the very closely related species homocysteine. The methods may be used, for example, in a direct assay of human blood plasma for homocysteine levels.