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Fmoc-Tyr(tBu)-OH

Fmoc-Tyr(tBu)-OH Basic information
Product Name:Fmoc-Tyr(tBu)-OH
Synonyms:FMOC-L-TYR(TBU)-OH(71989-38-3);(2S)-3-[4-(tert-butoxy)phenyl]-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;FMOC-L-TYROSINE(O-T-BUTYL);FMOC-L-TYROSINE (TBU);o-(tert-butyl)-n-[(9h-fluoren-9-ylmethoxy)carbonyl]-l-tyrosine;O-TERT-BUTYL-NALPHA-FMOC-L-TYROSINE;N-FMOC-T-BUTYL-L-TYR;N-FMOC-O-T-BUTYL-L-TYROSINE
CAS:71989-38-3
MF:C28H29NO5
MW:459.53
EINECS:276-262-7
Product Categories:Tyrosine [Tyr, Y];Amino Acid Derivatives;Fluorenes, Flurenones;Amino Acids;Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
Mol File:71989-38-3.mol
Fmoc-Tyr(tBu)-OH Structure
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)
pka2.97±0.10(Predicted)
form Powder
color White
optical activity[α]20/D 29±2°, c = 1% in DMF
BRN 4216652
InChIKeyJAUKCFULLJFBFN-VWLOTQADSA-N
SMILESC(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 Reference71989-38-3(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 Information
ProviderLanguage
Fmoc-O-tert-butyl-L-tyrosine English
SigmaAldrich English
Fmoc-Tyr(tBu)-OH Usage And Synthesis
Chemical Propertieswhite 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).
UsesFmoc-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.
PreparationTo 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 DescriptionFmoc-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 Preparation Products And Raw materials
Raw materials1,4-Dioxane-->Fluorene-->O-tert-Butyl-L-tyrosine
Preparation ProductsOxytocin-->ANGIOTENSIN I, HUMAN-->ANGIOTENSIN II, HUMAN-->FMOC-O-BUTYL-L-TYROSINE N-HYDROXYSUCCINIMIDE ESTER
L-Tyrosine H-ARG-ARG-LEU-ILE-GLU-ASP-ASN-GLU-TYR-THR-ALA-ARG-GLY-OH TYROSINASE Cyhalofop-butyl 4-tert-Butylphenol PYRAZOPHOS Fmoc-Aib-OH tert-Butyldimethylsilyl chloride tert-Butyl hydroperoxide Buprofezin Methyl 4-tert-butylbenzoate Fmoc-Tyr(tBu)-OH Butyl acrylate butyl rubber Butyl acetate 9-Fluorenylmethyl chloroformate Fmoc 2-Butoxyethanol
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