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47622

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:
Molecular Weight:
397.46
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
276-261-1
MDL number:
Beilstein/REAXYS Number:
4581133

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Product Name

Fmoc-Thr(tBu)-OH, ≥98.0% (HPLC)

SMILES string

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

InChI key

LZOLWEQBVPVDPR-VLIAUNLRSA-N

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

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

Quality Level

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This Item
473124762347311
functional group

Fmoc, carboxylic acid, amine

functional group

Fmoc

functional group

Fmoc

functional group

Fmoc

assay

≥98.0% (HPLC)

assay

≥98.0% (TLC)

assay

≥98.0% (HPLC)

assay

≥98.0% (TLC)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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

[α]20/D −29±2°, c = 1% in DMF

optical activity

-

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
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
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

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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