| Identification | More | [Name]
N-Cbz-L-Tryptophan | [CAS]
7432-21-5 | [Synonyms]
BENZYLOXYCARBONYL-L-TRYPTOPHAN
CBZ-L-TRYPTOPHAN
CBZ-TRP-OH
N-ALPHA-BENZYLOXYCARBONYL-L-TRYPTOPHAN
N-ALPHA-CARBOBENZOXY-L-TRYPTOPHAN
N-ALPHA-CARBOBENZYLOXY-L-TRYPTOPHAN
N(ALPHA)-CBZ-L-TRYPTOPHAN
N-BENZYLOXYCARBONYL-L-TRYPTOPHAN
N-CARBOBENZOXY-L-TRYPTOPHAN
N-CBZ-L-TRYPTOPHAN
N-CBZ-L-TRYPTOPHAN-OH
Z-L-TRP-OH
Z-L-TRYPTOPHAN
Z-TRP-OH
Z-TRYPTOPHAN
Nα-Carbobenzyloxy-L-tryptophan
N-α-Z-L-tryptophan
N(a)-Benzyloxycarbonyl-L-tryptophan
N-CBZ-L-TRYPTOPHAN CRYSTALLINE
CBZ-L-TRP-OH | [EINECS(EC#)]
231-074-4 | [Molecular Formula]
C19H18N2O4 | [MDL Number]
MFCD00065700 | [Molecular Weight]
338.36 | [MOL File]
7432-21-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
124-127 °C(lit.) | [alpha ]
2.5 º (c=3, EtOH) | [Boiling point ]
474.51°C (rough estimate) | [density ]
1.2855 (rough estimate) | [refractive index ]
1.6140 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
methanol: 0.1 g/mL, clear
| [form ]
Solid | [pka]
3.98±0.10(Predicted) | [color ]
White | [Optical Rotation]
[α]20/D +2.9±0.3°, c = 3% in acetic acid | [BRN ]
96743 | [CAS DataBase Reference]
7432-21-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
Nα-Cbz-L-tryptophan is an N-Cbz-protected form of L-Tryptophan (T947210). L-Tryptophan is an essential amino acid that is important for cell proliferation and the biosynthesis of proteins. It is a precursor to Serotonin (HCl: S274980), a neurotransmitter that compound that aids in sleep and mental state. L-Tryptophan is also thought to cause eosinophilia-myalgia syndrome. | [Synthesis]
L-tryptophan (10.24 g, 50 mmol) was dissolved in 1 M aqueous sodium hydroxide solution (50 mL) and stirred at 0 °C. Subsequently, benzyl chloroformate (7.15 mL, 50.1 mmol) was added slowly and dropwise into the reaction system simultaneously with 1 M aqueous sodium hydroxide solution (50 mL). After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was acidified to pH 1 with 6 M hydrochloric acid, and then the target product was extracted with ethyl acetate (3 x 200 mL). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give a yellow solid product (16.72 g, 99% yield), which could be used in the next reaction without further purification. The analytical data of the product were as follows: thin layer chromatography (TLC) Rf value of 0.43 (unfolding agent ratio of 95:4:1 dichloromethane/methanol/acetic acid); melting point (Mp): 132-134 °C; 1H NMR (DMSO-d6, 400 MHz) δ: 7.57-7.53 (m, 2H), 7.35-7.22 (m, 6H), 7.16- 7.15 (m, 1H), 7.09-7.04 (m, 1H), 7.00-6.95 (m, 1H), 5.02-4.92 (m, 2H), 4.28-4.21 (m, 1H), 3.22-3.16 (m, 1H), 3.04-2.96 (m, 1H); 13C NMR (DMSO-d6, 100 MHz) δ : 174.2, 156.5, 137.4, 136.6, 128.8, 128.2, 128.0, 127.6, 124.2, 121.4, 118.8, 118.6, 111.9, 110.5, 65.8, 55.5, 27.4; low resolution mass spectrometry (LRMS, ESI+): C19H19N2O4 [M+ H]+ calculated value 339.13, measured value 339.35. | [References]
[1] Tetrahedron Letters, 2012, vol. 53, # 47, p. 6430 - 6432
[2] Tetrahedron Letters, 2006, vol. 47, # 36, p. 6393 - 6396
[3] Synthesis, 1986, # 11, p. 958 - 960
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 3, p. 462 - 473
[5] Patent: CN105884674, 2016, A. Location in patent: Paragraph 0085; 0086; 0087 |
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