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Fmoc-Glu(OtBu)-OH

Name: Fmoc-Glu(OtBu)-OH
Brand: ALDRICH

≥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

Beilstein:

3636375

EC Number:

276-253-8

MDL number:

MFCD00037135

UNSPSC Code:

12352209

eCl@ss:

32160406

PubChem Substance ID:

57651045

NACRES:

NA.26

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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Amino Acids, Resins & Reagents for Peptide Synthesis

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 .

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)

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)

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)

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)

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