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47622

Sigma-Aldrich

Fmoc-Thr(tBu)-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

Fmoc-O-tert-butyl-L-threonine

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CN¥509.32
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CN¥2,060.75

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10 G
CN¥509.32
100 G
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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

CN¥509.32

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Product Name

Fmoc-Thr(tBu)-OH, ≥98.0% (HPLC)

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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1 of 4

This Item
473124751347911
Fmoc-Thr(tBu)-OH ≥98.0% (HPLC)

47622

Fmoc-Thr(tBu)-OH

Fmoc-D-Thr(tBu)-OH ≥98.0% (TLC)

47312

Fmoc-D-Thr(tBu)-OH

Fmoc-Thr(Bzl)-OH ≥98.0% (TLC)

47513

Fmoc-Thr(Bzl)-OH

Fmoc-β-Homothr(tBu)-OH ≥96.0% (HPLC)

47911

Fmoc-β-Homothr(tBu)-OH

assay

≥98.0% (HPLC)

assay

≥98.0% (TLC)

assay

≥98.0% (TLC)

assay

≥96.0% (HPLC)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

optical activity

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

optical activity

[α]20/D −15±1.5°, c = 1% in ethyl acetate

optical activity

-

optical activity

-

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

-

reaction suitability

reaction type: C-H Activation

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

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.[1] [2]

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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    BCCM6095
    BCCK7746
    BCCJ6585
    BCCH9521
    BCCH2943

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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
    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
    Michał Padjasek et al.
    Chemistry (Weinheim an der Bergstrasse, Germany), 26(15), 3297-3313 (2019-12-18)
    CdII is a major genotoxic agent that readily displaces ZnII in a multitude of zinc proteins, abrogates redox homeostasis, and deregulates cellular metalloproteome. To date, this displacement has been described mostly for cysteine(Cys)-rich intraprotein binding sites in certain zinc finger
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