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47625

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

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

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Properties

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

Description

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 .

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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 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)

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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Global Trade Item Number

SKU	GTIN
47625-25G	04061832362281
47625-100G	04061832362267
47625-10G	04061832362274
47625-1KG	04061826222713