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78539

Sigma-Aldrich

Boc-Tyr(Allyl)-OH

≥98.0% (HPLC)

Synonym(s):

Boc-O-allyl-L-tyrosine

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About This Item

Empirical Formula (Hill Notation):
C17H23NO5
CAS Number:
127132-38-1
Molecular Weight:
321.37
Beilstein:
3624582
MDL number:
MFCD00273424
UNSPSC Code:
12352209
PubChem Substance ID:
57652748
NACRES:
NA.22

Assay

≥98.0% (HPLC)

form

powder

reaction suitability

reaction type: Boc solid-phase peptide synthesis

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)N[C@@H](Cc1ccc(OCC=C)cc1)C(O)=O

InChI

1S/C17H23NO5/c1-5-10-22-13-8-6-12(7-9-13)11-14(15(19)20)18-16(21)23-17(2,3)4/h5-9,14H,1,10-11H2,2-4H3,(H,18,21)(H,19,20)/t14-/m0/s1

InChI key

YIRRNENSHUFZBH-AWEZNQCLSA-N

Application

Due to gem-dimethyl substituent effect, Boc-Tyr(Allyl)-OH is found to be resistant to Claisen rearrangement in water.

Other Notes

Allyl group side-chain protected tyrosine; building block for unnatural amino acids by metathesis reaction

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A Loffet et al.
International journal of peptide and protein research, 42(4), 346-351 (1993-10-01)
Allyl and allyloxycarbonyl groups are used for the side-chain protection of amino acids. The protecting groups may be selectively cleaved using the reagent HSnBu3 under palladium catalysis. The preparation of Boc and Fmoc series of protected amino acids is described.
Aromatic Claisen Rearrangements of O?Prenylated Tyrosine and Model Prenyl Aryl Ethers: Computational Study of the Role of Water on Acceleration of Claisen Rearrangements.
Osuna S, et al.
European Journal of Organic Chemistry, 2013(14), 2823-2831 (2013)
Angewandte Chemie (International Edition in English), 114, 2964-2964 (2002)

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