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Sigma-Aldrich

Fmoc-Thr(tBu)-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

Fmoc-O-tert-butyl-L-threonine

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About This Item

Empirical Formula (Hill Notation):
C23H27NO5
CAS Number:
71989-35-0
Molecular Weight:
397.46
Beilstein:
4581133
EC Number:
276-261-1
MDL number:
MFCD00077075
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57651042
NACRES:
NA.26

product name

Fmoc-Thr(tBu)-OH, ≥98.0% (HPLC)

Quality Level

100

Assay

≥98.0% (HPLC)

optical activity

[α]20/D +16±1°, c = 1% in ethyl acetate

reaction suitability

reaction type: C-H Activation
reaction type: Fmoc solid-phase peptide synthesis
reagent type: ligand
reaction type: Peptide Synthesis

application(s)

peptide synthesis

functional group

Fmoc
amine
carboxylic acid

storage temp.

2-8°C

SMILES string

C[C@@H](OC(C)(C)C)[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

InChI

1S/C23H27NO5/c1-14(29-23(2,3)4)20(21(25)26)24-22(27)28-13-19-17-11-7-5-9-15(17)16-10-6-8-12-18(16)19/h5-12,14,19-20H,13H2,1-4H3,(H,24,27)(H,25,26)/t14-,20+/m1/s1

InChI key

LZOLWEQBVPVDPR-VLIAUNLRSA-N

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General description

Fmoc-Thr(tBu)-OH also known as Fmoc-O-tert-butyl-L-threonine, is commonly used as amino acid building block in peptide synthesis.

Application

Fmoc-Thr(tBu)-OH can be used to synthesize chlorofusin analogues via solid phase peptide synthesis. Additionally, it can serve as a protecting group for both the amine and the hydroxyl functions in solid-phase synthesis of complex depsipeptides.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Solid-phase synthesis of chlorofusin analogues
ECY Woon
The Journal of Organic Chemistry, 72, 5146-5151 (2007)
General Fmoc-Based Solid-Phase Synthesis of Complex Depsipeptides Circumventing Problematic Fmoc Removal
A Lobo-Ruiz
European Journal of Organic Chemistry, 2020, 183-192 (2020)
Stefan Eissler et al.
Journal of peptide science : an official publication of the European Peptide Society, 23(10), 757-762 (2017-06-22)
In solid-phase peptide synthesis, the nominal batch size is calculated using the starting resin substitution and the mass of the starting resin. The starting resin substitution constitutes the basis for the calculation of a whole set of important process parameters
Gizella Csire et al.
Journal of inorganic biochemistry, 203, 110927-110927 (2019-12-07)
Interaction of copper(II) and nickel(II) ions with the Ac-PHAAAGTHSMKHM-NH2 tridecapeptide containing the His85, His96 and His111 binding sites of human prion protein has been studied by various techniques. pH-potentiometry, UV-Vis and circular dichroism spectroscopy were applied to study the stoichiometry
Zdenek Kukacka et al.
ChemMedChem, 13(9), 909-915 (2018-02-24)
α-Galactosidase (αGal) is a lysosomal enzyme that hydrolyses the terminal α-galactosyl moiety from glycosphingolipids. Mutations in the encoding genes for αGal lead to defective or misfolded enzyme, which results in substrate accumulation and subsequent organ dysfunction. The metabolic disease caused
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