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8.52085

Fmoc-Glu(O-2-PhiPr)-OH

Name: Fmoc-Glu(O-2-PhiPr)-OH
Brand: MM

≥97% (TLC), for peptide synthesis, Novabiochem^®

Synonym(s):

Fmoc-Glu(O-2-PhiPr)-OH, N-α-Fmoc-L-glutamic acid γ-2-phenylisopropyl ester

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₂₉NO₆

CAS Number:

200616-39-3

Molecular Weight:

487.54

MDL number:

MFCD00672323

UNSPSC Code:

12352209

NACRES:

NA.22

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Properties

Product Name

Fmoc-Glu(O-2-PhiPr)-OH, Novabiochem^®

Quality Segment

200

product line

Novabiochem^®

assay

≥90.0% (acidimetric), ≥95.0% (HPLC), ≥97% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem^®

application(s)

peptide synthesis

functional group

carboxylic acid

storage temp.

15-25°C

SMILES string

N([C@@H](CCC(=O)OC(C)(C)c4ccccc4)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3

InChI

1S/C29H29NO6/c1-29(2,19-10-4-3-5-11-19)36-26(31)17-16-25(27(32)33)30-28(34)35-18-24-22-14-8-6-12-20(22)21-13-7-9-15-23(21)24/h3-15,24-25H,16-18H2,1-2H3,(H,30,34)(H,32,33)/t25-/m0/s1

InChI key

NPNRKQDJIWMHNG-VWLOTQADSA-N

Description

General description

Quasi-orthogonally-protected Glu derivative. The 2-PhiPr group can be removed selectively in the presence of tBu-based protecting groups by treatment with 1% TFA in DCM ^[1], making this derivative an extremely useful tool for the preparation of cyclic peptides by Fmoc SPPS ^[2] or for library synthesis. For the on-resin synthesis of side-chain to side-chain lactam bridged peptides, the combination of Lys(Mtt) and Glu(O-2-PhiPr) is particularly advantageous since both side-chains can be simultaneously unmasked in a single step.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] C. Yue, et al. (1993) Tetrahedron Lett., 34, 323.
^[2] F. Dick, et al. in ′Peptides 1996, Proc. of 24th European Peptide Symposium′, R. Ramage & R. Epton (Eds), Mayflower Scientific Ltd., Birmingham, 1998, pp. 339.

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.0 % (a/a)
Purity (TLC(011A)): ≥ 97 %
Purity (TLC(0811)): ≥ 97 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 90.0 %
Water (K. F.): ≤ 2.0 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Other Notes

Replaces: 04-12-1199

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c