Fmoc-Gly-Gly-OH Chemical Properties

Melting point:

176-177 °C

Boiling point:

684.1±45.0 °C(Predicted)

Density 

1.338±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

pka

3.39±0.10(Predicted)

form 

Powder

color 

White

InChI

InChI=1S/C19H18N2O5/c22-17(20-10-18(23)24)9-21-19(25)26-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2,(H,20,22)(H,21,25)(H,23,24)

InChIKey

FBKUOPULLUJMOC-UHFFFAOYSA-N

SMILES

C(O)(=O)CNC(=O)CNC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O

Safety Information

WGK Germany 

WGK 3

HS Code 

2924297099

Storage Class

11 - Combustible Solids

Fmoc-Gly-Gly-OH Usage And Synthesis

Description

Fmoc-Gly-Gly-OH is a peptide linker. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations.

Chemical Properties

White powder

Uses

Fmoc-Gly-Gly-OH is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs)[1].

Synthesis

General procedure for the synthesis of N-fluorenylmethoxycarbonyl-glycyl-glycine from bisglycopeptide and chloroformic acid-9-fluorenylmethyl ester: 15 mL of dioxane was added to a mixture of bisglycopeptide (1 mmol) and chloroformic acid-9-fluorenylmethyl ester (1.2 mmol), cooled to 0 °C and then an equal volume of a 1N Na2CO3 solution was slowly added. The reaction mixture was stirred at room temperature for 12 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction solution was acidified to pH 4-5 with 1 M HCl. The reaction mixture was extracted with ethyl acetate (3 x 70 mL) at 0 °C. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford pure N-fluorenylmethoxycarbonyl-glycyl-glycine in 89% yield.

IC 50

Cleavable Linker

References

[1] Beck A, et al. Strategies and challenges for the next generation of antibody-drug conjugates. Nat Rev Drug Discov. 2017 May;16(5):315-337. DOI:10.1038/nrd.2016.268

Fmoc-Gly-Gly-OH(35665-38-4)Related Product Information

• 4-Hydroxy-D-(-)-2-phenylglycine
• Fmoc-Aib-OH
• 4-Aminophenylacetic acid
• Glycine
• N-Carbobenzyloxyglycine
• Glycylglycine
• 9-Fluorenylmethyl chloroformate
• METHOXYFENOZIDE
• Fmoc-Gly-OH
• Fmoc-OSu
• Fmoc
• FMOC-ALA-ALA-OH
• Fmoc-Pro-Pro-OH
• FMOC-LYS(BOC)-LEU-OH
• FMOC-ALA-PRO-OH
• FMOC-NLE-NLE-OH
• FMOC-SER(TBU)-THR(TBU)-OH
• FMOC-PHE-ARG-OH