BOC-L-Tyrosine Chemical Properties

Melting point:

133-135 °C(lit.)

alpha 

2.5 º (c=2, acetic acid)

Boiling point:

423.97°C (rough estimate)

Density 

1.1755 (rough estimate)

refractive index 

1.5230 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Sparingly)

pka

2.98±0.10(Predicted)

form 

Powder

color 

White to off-white

optical activity

[α]20/D +3.0°, c = 2 in acetic acid

BRN 

2816406

Major Application

peptide synthesis

InChI

InChI=1S/C14H19NO5/c1-14(2,3)20-13(19)15-11(12(17)18)8-9-4-6-10(16)7-5-9/h4-7,11,16H,8H2,1-3H3,(H,15,19)(H,17,18)/t11-/m0/s1

InChIKey

CNBUSIJNWNXLQQ-NSHDSACASA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(O)C=C1)NC(OC(C)(C)C)=O

CAS DataBase Reference

3978-80-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HS Code 

29242990

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:BOC-L-Tyrosine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

BOC-L-Tyrosine Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

N-Boc-L-tyrosine is an N-Boc-protected form of L-Tyrosine (T899975). L-Tyrosine is an essential amino acid that exhibits in vitro antioxidant and antiradical activities. L-Tyrosine is used as a precursor to synthesize catecholamines (e.g. Norepinephrine HCl [N674500]) in human keratinocytes, and also for the synthesis of proteins and thyroid hormones.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

In a dry 50 mL round-bottomed flask, (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid ( 200 mg) was dissolved in dry 1,4 -dioxane ( 10 mL) and H2O (5 mL) ( 2:1 ). NaOH ( 1 M, 5 mL, 5 mmol, 4.5 eq.) and Boc2O ( 0.28 mL, 1.21 mmol) were then added sequentially to the solution. The resulting reaction mixture was stirred at room temperature for 3 h. The progress of the reaction was monitored by LCMS and after waiting for the end of the reaction the reaction solution was acidified with 2 M HCl to a pH of about 2 - 3. The resulting reaction mixture was extracted three times with ethyl acetate ( 3 ?? 25 mL), all the organic layers were combined and the organic layer was washed with brine, the organic layer was separated out and dried with anhydrous Na2SO4, the organic layer was filtered to remove the drying agent, and the resulting organic layer was dried with anhydrous Na2SO4. The organic layer was separated and dried with anhydrous Na2SO4, the organic layer was filtered to remove the desiccant, and the resulting filtrate was concentrated under vacuum to remove the organic solvent, and the crude product was separated and purified by silica gel column chromatography to obtain the target product molecule, N-tert-butoxycarbonyl-L-tyrosine.

BOC-L-Tyrosine(3978-80-1)Related Product Information

• N-[(tert-Butoxy)carbonyl]-L-tryptophan
• Boc-Aib-OH
• N-BOC-1,6-diaminohexane
• BOC-METYR(ME)-OH DCHA
• N-Boc-Ethylenediamine
• BOC-L-TYROSINE(2-BROMOCBZ)
• Boc-O-benzyl-L-tyrosine
• BOC-TYR(2,6-DI-CL-BZL)-OH
• Boc-Tyr(Me)-OH
• BOC-L-Tyrosine
• BOC-TYR(ET)-OH
• N-tert-Butyloxycarbonyl-N-methyl-O-benzyl-L-threonine
• Boc-L-tyrosine methyl ester, N-(tert-Butoxycarbonyl)-L-tyrosine methyl ester,BOC-L-TYROSINE METHYL ESTER,N-BOC-L-TYROSINE METHYL ESTER
• Boc-D-Tyr-OH
• BOC-D-TYROSINE(2-BROMO-Z)-OH
• BOC-L-TYROSINE ETHYL ESTER
• BOC-D-TYROSINE(BZL)-OH
• BOC-D-TYROSINE(ET)-OH