Skip to Content
MilliporeSigma
All Photos(1)

Documents

8.52102

Sigma-Aldrich

Fmoc-Glu(biotinyl-PEG)-OH

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

Synonym(s):

Fmoc-Glu(biotinyl-PEG)-OH, N-α-Fmoc-N-γ-(N-biotinyl-3-(2-(2-(3-aminopropyloxy)-ethoxy)-ethoxy)-propyl)-L-glutamine

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C40H55N5O10S
CAS Number:
Molecular Weight:
797.96
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22

product name

Fmoc-Glu(biotinyl-PEG)-OH, Novabiochem®

Quality Level

product line

Novabiochem®

assay

≥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

biotin

storage temp.

2-8°C

InChI

1S/C40H55N5O10S/c46-35(14-6-5-13-34-37-33(26-56-34)43-39(50)45-37)41-17-7-19-52-21-23-54-24-22-53-20-8-18-42-36(47)16-15-32(38(48)49)44-40(51)55-25-31-29-11-3-1-9-27(29)28-10-2-4-12-30(28)31/h1-4,9-12,31-34,37H,5-8,13-26H2,(H,41,46)(H,42,47)(H,44,51)(H,48,49)(H2,43,45,50)/t32-,33-,34-,37-/m0/s1

InChI key

MGOWNVYDCIBVKC-FNHRVDEZSA-N

General description

In contrast to Fmoc-Lys(biotin)-OH, this novel biotin-labeled amino acid has excellent solubility in DMF and other solvents used in Fmoc SPPS [1]. The PEG-spacer restricts hindrance between the peptide and avidin, leading to better biotin binding. Furthermore, the hydrophilic nature of the PEG minimizes non-specific interactions that can arise from the spacer group becoming buried in the hydrophobic pocket of proteins.For recent applications, please see [2,3,4].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Biotinylation Reagents for Peptide Synthesis


Literature references

[1] B. Baumeister, et al. (2003) Biopolymers, 71, 339.
[2] X. Zhou et al., (2004) J. Am. Chem. Soc., 126, 15656.
[3] B. F. Gilmore, et al. (2006) Biochem. Biophys. Res. Commun,, 347, 373.
[4] C. T. Archer, et al. (2005) Mol. BioSyst., 1, 366.

Application

  • Unbiased peptoid combinatorial cell screen identifies plectin protein as a potential biomarker for lung cancer stem cells: Utilized Fmoc-Glu(biotinyl-PEG)-OH in the synthesis protocol for peptoid libraries, contributing to biomarker discovery in lung cancer research (AC Raymond et al., 2019).
  • Identification of side arm-modified DOTA scaffolds as multi-site binding ligands for cancer cells over normal cells: Included Fmoc-Glu(biotinyl-PEG)-OH in a synthesis protocol to enhance biotinylated scaffold properties for selective cancer cell targeting (V Rustagi, DG Udugamasooriya, 2019).
  • TANGO-inspired design of anti-amyloid cyclic peptides: Employed Fmoc-Glu(biotinyl-PEG)-OH in the synthesis of cyclic peptides aimed at studying amyloid protein interactions, crucial for Alzheimer′s disease research (X Lu, RM Murphy, 2016).
  • Converting a weaker ATP-binding site inhibitor into a potent hetero-bivalent ligand by tethering to a unique peptide sequence derived from the same kinase: Used Fmoc-Glu(biotinyl-PEG)-OH in developing new kinase inhibitors with improved binding properties (SR Kedika, DG Udugamasooriya, 2018).

Linkage

Replaces: 04-12-1250

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(CMA2)): ≥ 97 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (0,2 mmol in 1 ml DMF): clearly soluble

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

Legal Information

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2


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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Related Content

Biotin-labelled peptides have many important applications in immunology and histochemistry, such as affinity purification and FRET-based flow cytometry, solid-phase immunoassays, and receptor localization, that exploit the high affinity of streptavidin and avidin for biotin.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service