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47625

Sigma-Aldrich

Fmoc-Glu(OtBu)-OH

≥98.0% (HPLC)

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Synonym(s):
Fmoc-L-glutamic acid 5-tert-butyl ester
Empirical Formula (Hill Notation):
C24H27NO6
CAS Number:
Molecular Weight:
425.47
Beilstein:
3636375
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

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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1 of 4

This Item
477031543647618
Fmoc-Glu(OtBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47625

Fmoc-Glu(OtBu)-OH

Fmoc-Glu(OAll)-OH ≥96.0% (HPLC)

Sigma-Aldrich

47703

Fmoc-Glu(OAll)-OH

Boc-Glu(OtBu)-OH ≥99.0% (sum of enantiomers, TLC)

Sigma-Aldrich

15436

Boc-Glu(OtBu)-OH

Fmoc-Asp(OtBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47618

Fmoc-Asp(OtBu)-OH

form

powder

form

-

form

powder

form

powder

optical activity

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

optical activity

[α]20/D −16.5±2°, c = 1% in DMF

optical activity

[α]20/D −9.5±1°, c = 1% in methanol

optical activity

[α]20/D −24±2°, c = 1% in DMF

impurities

~4% water

impurities

-

impurities

-

impurities

-

functional group

Fmoc

functional group

Fmoc

functional group

-

functional group

Fmoc

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

General description

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

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 .

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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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)
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)
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)
Stapled α-helical peptide drug development: A potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy
Chang YS, et al.
Proceedings of the National Academy of Sciences of the USA, 110(36), E3445-E3454 (2013)

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