[ CAS No. 56-89-3 ]

Name: 56-89-3|(2R,2'R)-3,3'-Disulfanediylbis(2-aminopropanoic acid)|98%
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SKU: A160767
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{[proInfo.proName]} (Synonyms:L-Cystine) ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D

3d Animation Molecule Structure of 56-89-3

Structure of 56-89-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 56-89-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 56-89-3 ]

SDS Specification

Alternatived Products of [ 56-89-3 ]

Product Details of [ 56-89-3 ]

CAS No. :	56-89-3	MDL No. :
Formula :	-	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	-	Pubchem ID :	-
Synonyms :	L-Cystine

Calculated chemistry of [ 56-89-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	7
Num. H-bond acceptors :	6.0
Num. H-bond donors :	4.0
Molar Refractivity :	55.1
TPSA :	177.24 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-11.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.51
Log Po/w (XLOGP3) :	-5.08
Log Po/w (WLOGP) :	-0.81
Log Po/w (MLOGP) :	-5.83
Log Po/w (SILICOS-IT) :	-1.33
Consensus Log Po/w :	-2.51

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	2.33
Solubility :	51700.0 mg/ml ; 215.0 mol/l
Class :	Highly soluble
Log S (Ali) :	2.0
Solubility :	23900.0 mg/ml ; 99.6 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.95
Solubility :	2170.0 mg/ml ; 9.02 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.39

Safety of [ 56-89-3 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 56-89-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 56-89-3 ]
Downstream synthetic route of [ 56-89-3 ]

[ 56-89-3 ] Synthesis Path-Upstream 1~18

1
[ 56-89-3 ]
[ 6601-20-3 ]
[ 2150-55-2 ]

Reference： [1] Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2071 - 2076

2
[ 56-89-3 ]
[ 57-06-7 ]
[ 6601-20-3 ]
[ 2150-55-2 ]

Reference： [1] Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2071 - 2076

3
[ 56-89-3 ]
[ 151-50-8 ]
[ 2150-55-2 ]

Reference： [1] Monatshefte fuer Chemie, 1957, vol. 88, p. 478,492

4
[ 56-89-3 ]
[ 57-06-7 ]
[ 2150-55-2 ]

Reference： [1] Agricultural and Biological Chemistry, 1983, vol. 47, # 9, p. 2071 - 2076

5
[ 56-89-3 ]
[ 108-24-7 ]
[ 616-91-1 ]

Reference： [1] Biochemical Journal, 1931, vol. 25, p. 619
[2] Biochemical Journal, 1933, vol. 27, p. 1716

6
[ 463-51-4 ]
[ 56-89-3 ]
[ 616-91-1 ]

Reference： [1] Biochemical Journal, 1931, vol. 25, p. 619
[2] Biochemical Journal, 1933, vol. 27, p. 1716

7
[ 56-89-3 ]
[ 3054-01-1 ]

Reference： [1] Journal of Biological Chemistry, 1939, vol. 130, p. 109,111
[2] Journal of the American Chemical Society, 1930, vol. 52, p. 4500,4503

8
[ 56-89-3 ]
[ 501-53-1 ]
[ 6968-11-2 ]

Reference： [1] Canadian Journal of Chemistry, 2007, vol. 85, # 3, p. 164 - 174
[2] Journal of the American Chemical Society, 2012, vol. 134, # 9, p. 4112 - 4115
[3] Tetrahedron, 1996, vol. 52, # 29, p. 9823 - 9834
[4] Journal of Heterocyclic Chemistry, 2000, vol. 37, # 6, p. 1463 - 1469
[5] Tetrahedron, 1992, vol. 48, # 5, p. 931 - 938
[6] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 503 - 510
[7] Chemische Berichte, 1932, vol. 65, p. 1192,1198
[8] Biochemical Preparations, 1952, vol. 2, p. 74,75
[9] Die Pharmazie, 1969, vol. 24, # 6, p. 305 - 308
[10] Canadian Journal of Chemistry, 1981, vol. 59, # 2, p. 406 - 421
[11] Journal of Organic Chemistry, 1999, vol. 64, # 4, p. 1420 - 1423

9
[ 56-89-3 ]
[ 91285-94-8 ]
[ 6968-11-2 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575

10
[ 56-89-3 ]
[ 96452-48-1 ]
[ 6968-11-2 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575

11
[ 56-89-3 ]
[ 6968-11-2 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1956, vol. 29, p. 664,668

12
[ 56-89-3 ]
[ 7732-18-5 ]
[ 611-73-4 ]
[ 3342-78-7 ]

Reference： [1] Journal of the American Chemical Society, 1936, vol. 58, p. 2241

13
[ 56-89-3 ]
[ 10318-18-0 ]

Reference： [1] Synthetic Communications, 1989, vol. 19, # 18, p. 3143 - 3150

14
[ 67-56-1 ]
[ 56-89-3 ]
[ 32854-09-4 ]

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 6, p. 1132 - 1135
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 7, p. 2373 - 2379
[3] Chemical Communications, 2015, vol. 51, # 39, p. 8245 - 8248
[4] Chemical Communications, 2013, vol. 49, # 48, p. 5507 - 5509
[5] RSC Advances, 2014, vol. 4, # 11, p. 5322 - 5328
[6] Tetrahedron, 2010, vol. 66, # 22, p. 3923 - 3929
[7] Patent: WO2011/62640, 2011, A1, . Location in patent: Page/Page column 37; 38
[8] New Journal of Chemistry, 2016, vol. 40, # 10, p. 8382 - 8389
[9] Patent: US2018/305307, 2018, A1, . Location in patent: Paragraph 0315

15
[ 540-88-5 ]
[ 56-89-3 ]
[ 38261-78-8 ]

Reference： [1] Chemische Berichte, 1994, vol. 127, # 7, p. 1235 - 1242

16
[ 56-89-3 ]
[ 28920-43-6 ]
[ 135273-01-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium carbonate In 1,4-dioxane; water at 10 - 20℃; for 2 h;	Sodium carbonate (4.6 g, 43.6 mmol) and L-cystine (5.0 g, 20.8 mmol) were dissolved in water (200 mL). The resulting solution was cooled to 10° C. FmocCl (11.85 g, 45.8 mmol) was dissolved in dioxane (80 mL), and the resulting solution was added dropwise to the aqueous solution of L-cystine. The solution was stirred for 2 h at 10° C. and allowed to gradually warm to room temperature. A thick white precipitate was obtained that was filtered onto a sintered glass funnel. The product was triturated with diethyl ether (50 mL) and dried in vacuuo for 2 d. N,N'-Bis(Fmoc)-L-cystine (14.0 g, 98percent yield) was obtained as a white powder.

Reference： [1] Patent: US2007/37963, 2007, A1, . Location in patent: Page/Page column 11-12; Figure 4

17
[ 56-89-3 ]
[ 82911-69-1 ]
[ 135273-01-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium carbonate In water; acetone at 50℃;	General procedure: Procedure adapted from that of Agan et al[28]. 407 mg Na₂CO₃ (3.82 mmol) was dissolved in 30 mL distilled water with stirring. 35 mL acetone was then added followed by 1.91 mmol L-cystine or L-selenocystine. The temperature of the reaction was brought to 50 °C and 1.93g (5.73 mmol) Fmoc-OSu was added in portions over 5 minutes. Heating was removed and the reaction was allowed to progress overnight. At the end of this time, 40 mL 1 HCl was added followed by 50 mL EtOAc. Following vigorous shaking, the layers were separated, and the organic portionwas dried over MgSO₄ and concentrated in vacuo to afford the crude bis N-Fmoc dichalcogenide which was purified by recrystallization from CHCl₃.

Reference： [1] Protein and Peptide Letters, 2014, vol. 21, # 12, p. 1257 - 1264

18
[ 540-88-5 ]
[ 56-89-3 ]
[ 82911-69-1 ]
[ 139592-37-3 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 19, p. 6074 - 6078
[2] Organic Letters, 2016, vol. 18, # 23, p. 6188 - 6191

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Yield	Reaction Conditions	Operation in experiment
97%	With thionyl chloride; at 65 - 70℃; for 16h;Large scale;	To generate the diNACA, Step 1 (01NPI01-01) was performed in a 2000L glass-lined reactor using 67 kg of L-cystine. The material was treated with methanol (1323 kg, 25 vol) and thionyl chloride (80 kg, 2.41 eq) and agitated for 1 hour before heating to reflux. Once the In-Process Control (IPC) sample met the criteria of less than 1% of L-cystine remaining, the reaction was deemed complete. After cooling to 20±5 C. the methanol was exchanged with methyl t-butylether and the product isolated by filtration. Due to the scale, the isolation occurred in three portions with the first and some of the second portion being carried forward without drying. The remainder of the material was dried under vacuum to yield L-cystine dimethylester dihydrochloride.
95.9%	With thionyl chloride; at -10℃; for 16h;Reflux; Large scale;	Set-up: A 2000 L glass-lined reactor; 50 kg L-Cystine; and 625 L Methanol was charged to the reactor and agitated while cooling to -10 C. 60 kg Thionyl Chloride was slowly added at ?-5 C. After addition completion, the reaction material was heated to reflux and held for 16 hours. After the reaction was verified as complete by HPLC (?0.5% starting material), the reaction was cooled to room temperature. The reaction mixture was concentrated to 6 volumes before solvent-exchanging into 3×8 volumes MTBE. The resulting slurry was agitated at room temperature for 1 hour before being filtered and washed with MTBE. The solids were dried at 45 C. under vacuum. Yield: 68.15 kg (95.9%), Purity: 95.8%
	With hydrogenchloride; at 0 - 20℃;	Compound 2 Synthesis of cystine dimethyl ester dihydrochioride (CDME)[00261] A stream of dry hydrogen chloride gas was sparged rapidly into a suspension of cystine(10 g) in anhydrous methanol (50 mL) and agitated with a magnetic stirrer. After all the cystine had dissolved the warm solution was cooled in an ice bath, and sparging of HC1 continued to saturation at 0- 5C. The reaction mixture was protected from atmospheric moisture with a calcium chloride drying tube and allowed to stand at room temperature for 3 hours. Solvent was removed from the reaction mixture under reduced pressure on a o rotary evaporator with the water bath set at 50C. An aliquot of methanol (50 mL) was added to the resulting syrup and then concentration by rotary evaporation repeated. To the dry syrupy residue was added anhydrous ether (20 mL) resulting in spontaneous crystallization. The mixture was allowed to stand overnight at 4C and the resulting crystalline suspension was collected by filtration in a buchner funnel and washed with cold anhydrous ether (30 mL). The filter cake was dried under reduced pressure over potassium hydroxide pellets in a desiccator.

Yield	Reaction Conditions	Operation in experiment
	In ammonium hydroxide; water; O-methylisourea hemisulfate;	Example 11 Synthesis of guanidino-L-cystine To a solution of cystine (1 gm, 4.2 mmol) in ammonium hydroxide (10 mL) in a screw-capped vial was added O-methylisourea hydrogen sulfate (1.8 gm, 10 mmol). The vial was sealed and heated to 60 C. for 16 h. The solution was then cooled and the ammonium hydroxide was removed by rotary evaporation. The solid was then dissolved in water (20 mL), filtered through a cotton plug. The product was then isolated by ion exchange chromatography using Bio-Rex 70 resin and eluding with hydrochloric acid (100 mM).
	In ammonium hydroxide; water; O-methylisourea hemisulfate;	Example 21 Synthesis of Guanidino-L-cystine To a solution of cystine (1 gm, 4.2 mmol) in ammonium hydroxide (10 mL) in a screw-capped vial was added O-methylisourea hydrogen sulfate (1.8 gm, 10 mmol). The vial was sealed and heated to 60 C. for 16 h. The solution was then cooled and the ammonium hydroxide was removed by rotary evaporation. The solid was then dissolved in water (20 mL), filtered through a cotton plug. The product was then isolated by ion exchange chromatography using Bio-Rex 70 resin and eluding with hydrochloric acid (100 mM).

Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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H220	Extremely flammable gas
H221	Flammable gas
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Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
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H310	Fatal in contact with skin
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H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
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H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
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H330	Fatal if inhaled
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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 56-89-3 ]

Quality Control of [ 56-89-3 ]

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Product Details of [ 56-89-3 ]

Calculated chemistry of [ 56-89-3 ]

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Medicinal Chemistry

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[ 56-89-3 ] Synthesis Path-Upstream 1~18

[ 56-89-3 ] Synthesis Path-Downstream 1~69

Similar Product of [ 56-89-3 ]

Related Functional Groups of [ 56-89-3 ]

Amino Acid Derivatives

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[ 56-89-3 ]

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[ 56-89-3 ]