N-Cbz-L-Tryptophan Chemical Properties

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. 

Inert atmosphere,2-8°C

solubility 

methanol: 0.1 g/mL, clear

pka

3.98±0.10(Predicted)

form 

Solid

color 

White

optical activity

[α]20/D +2.9±0.3°, c = 3% in acetic acid

BRN 

96743

CAS DataBase Reference

7432-21-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:N-Benzyloxycarbonyl-L-tryptophane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-Cbz-L-Tryptophan Usage And Synthesis

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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