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Sigma-Aldrich

Fmoc-Glu(OtBu)-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

Fmoc-L-glutamic acid 5-tert-butyl ester

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About This Item

Empirical Formula (Hill Notation):
C24H27NO6
CAS Number:
Molecular Weight:
425.47
Beilstein:
3636375
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
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Product Name

Fmoc-Glu(OtBu)-OH, ≥98.0% (HPLC)

Assay

≥98.0% (HPLC)

form

powder

optical activity

[α]20/D −5.0±2.0°, c = 1% in acetic acid: water (4:1)

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

impurities

~4% water

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

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

InChI

1S/C24H27NO6/c1-24(2,3)31-21(26)13-12-20(22(27)28)25-23(29)30-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,25,29)(H,27,28)/t20-/m0/s1

InChI key

OTKXCALUHMPIGM-FQEVSTJZSA-N

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General description

Fmoc-Glu(OtBu)-OH is widely used as a building block in peptide synthesis for the protection of amine groups.[1][2]

Application

Fmoc-Glu(OtBu)-OH (Fmoc-L-glutamic acid 5-tert-butyl ester) can be employed as a:
  • Ligand in the synthesis of cis-substituted cyclopropane carboxylic acids via C-H activation of cyclopropane carboxamides using Pd catalyst.[3]
  • Linker in the preparation of multi-small molecule-conjugated PTX (paclitaxel) derivatives.[4]

It can be also used as a building block in the preparation of stapled α-helical peptides [5], and peptide C-terminal thioesters [6].

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)

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Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry
Ingenito R, et al.
Journal of the American Chemical Society, 121(49), 11369-11374 (1999)
Multi-small molecule conjugations as new targeted delivery carriers for tumor therapy
Shan L, et al.
International journal of nanomedicine, 10(49), 5571-5571 (2015)
Spectral characterization, solvation effects on topological aspects, and biological attributes of Fmoc-L-glutamic acid 5-tert-butyl ester: An effective reagent in anticancer evaluations
Thirunavukkarasu M, et al.
Journal of Molecular Structure, 1269, 133793-133793 (2022)
Pd (II)-catalyzed enantioselective C-H activation of cyclopropanes
Wasa M, et al.
Journal of the American Chemical Society, 133(49), 19598-19601 (2011)
Synthesis of peptides from alpha-and beta-tubulin containing glutamic acid side-chain linked oligo-glu with defined length
Tegge W, et al.
International Journal of Peptides, 2010 (2010)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    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/449/386/product-dating-information-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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