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Merck
CN

47625

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:
71989-18-9
Molecular Weight:
425.47
NACRES:
NA.26
PubChem Substance ID:
57651045
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
276-253-8
MDL number:
MFCD00037135
Beilstein/REAXYS Number:
3636375

Key Documents

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Product Name

Fmoc-Glu(OtBu)-OH, ≥98.0% (HPLC)

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

SMILES string

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

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

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Related Categories

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.
  • Linker in the preparation of multi-small molecule-conjugated PTX (paclitaxel) derivatives.

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

General description

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

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBF6550V
WXBF5309V
WXBF3691V
WXBF3234V
WXBF1077V

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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)
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)
Pd (II)-catalyzed enantioselective C-H activation of cyclopropanes
Wasa M, et al.
Journal of the American Chemical Society, 133(49), 19598-19601 (2011)
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