8.52102

Fmoc-Glu(biotinyl-PEG)-OH

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
• Empirical Formula (Hill Notation): C₄₀H₅₅N₅O₁₀S
• CAS Number: 817169-73-6
• Molecular Weight: 797.96
• MDL number: MFCD18782826
• UNSPSC Code: 12352209

Properties

• Quality Level: 200
• 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

Description

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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2