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8.52102

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

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About This Item

Empirical Formula (Hill Notation):
C40H55N5O10S
CAS Number:
817169-73-6
Molecular Weight:
797.96
UNSPSC Code:
12352209
NACRES:
NA.22
MDL number:
MFCD18782826
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Product Name

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

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

SMILES string

S1[C@H]([C@H]5NC(=O)N[C@H]5C1)CCCCC(=O)NCCCOCCOCCOCCCNC(=O)CC[C@H](NC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O

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).

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.

Other Notes

Replaces: 04-12-1250

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

Certificates of Analysis (COA)

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