Fmoc-Tyr(tBu)-OH Chemical Properties

Melting point:

~150 °C (dec.)

alpha 

-28 º (c=1, DMF)

Boiling point:

658.2±55.0 °C(Predicted)

Density 

1.218±0.06 g/cm3(Predicted)

refractive index 

-30 ° (C=1, DMF)

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly), DMF (Slightly), Methanol (Slightly)

form 

Powder

pka

2.97±0.10(Predicted)

color 

White

optical activity

[α]20/D 29±2°, c = 1% in DMF

BRN 

4216652

InChIKey

JAUKCFULLJFBFN-VWLOTQADSA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(OC(C)(C)C)C=C1)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O

CAS DataBase Reference

71989-38-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

HS Code 

2924 29 70

MSDS

• Language:English Provider:Fmoc-O-tert-butyl-L-tyrosine
• Language:English Provider:SigmaAldrich

Fmoc-Tyr(tBu)-OH Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder; insoluble in water and petroleum ether, soluble in ethyl acetate, methanol and DMF; mp is 150-151°C; specific optical rotation [α] 20D + 5.2° (0.5-2.0mg/ml, ethyl acetate ), [α]20D-27.6° (0.5-2.0 mg/ml, DMF), [α]20D-6° (0.5-2.0 mg/ml, methanol).

Uses

Fmoc-O-tert-butyl-L-tyrosine belongs to L-tyrosine compounds. Its molecular structure contains a chiral center, so it can exist two enantiomers and has optical activity. Fmoc-Tyr(tBu)-OH is used in peptide synthesis as amino acid protection monomer.

Preparation

To obtain Fmoc-Tyr(tBu)-OH, the following steps are carried out:
Suspend O-tert-butyl-L-tyrosine in a solution of dioxane.
Conduct an acylation reaction with fluorenyl methaneoxycarbonyl azide.
After the reaction, extract the crude product with ethyl acetate under pH 9-10 conditions.
Purify the extracted product through recrystallization.
This process results in the final product, Fmoc-Tyr(tBu)-OH.

General Description

Fmoc-Tyr(tBu)-OH is the preferred tyrosine derivative for solid phase peptide synthesis by Fmoc protocols. Protecting the Tyr sidechain may not be essential in the synthesis of small peptides. If the phenolic functional group of tyrosine does become acylated during a coupling reaction, the subsequent treatment with piperdine to remove Fmoc-groups will also remove any acylation of the phenolic function. Using Fmoc-Tyr(tBu)-OH in peptide synthesis is more efficient, however, since none of the activated amino acids are used unproductively in acylating exposed tyrosine side-chains. The use of Fmoc-Tyr(tBu)-OH also eliminates all potential for side products arising from the acylation of the tyrosine side-chain.

Fmoc-Tyr(tBu)-OH(71989-38-3)Related Product Information

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