FMOC-GAMMA-ABU-OH Chemical Properties

Melting point:

172.0 to 176.0 °C

Boiling point:

571.9±33.0 °C(Predicted)

Density 

1.256±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.68±0.10(Predicted)

form 

Powder

color 

White

Water Solubility 

Slightly soluble in water.

BRN 

7491485

InChI

InChI=1S/C19H19NO4/c21-18(22)10-5-11-20-19(23)24-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17H,5,10-12H2,(H,20,23)(H,21,22)

InChIKey

ACUIFAAXWDLLTR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

116821-47-7(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

FMOC-GAMMA-ABU-OH Usage And Synthesis

Description

Fmoc-4-aminobutanoic acid can be used as a PROTAC linker in the synthesis of PROTACs and other conjugation applications. Fmoc-4-aminobutanoic acid is an alkane chian with terminal Fmoc-protected amine and carboxylic acid groups. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Chemical Properties

White powder

Uses

4-(Fmoc-amino)butyric acid is used in agrochemical, pharmaceutical and dyestuff field.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

At room temperature, γ-aminobutyric acid (2.00 g, 19.4 mmol) was dissolved in 14 mL of 10% NaHCO3 aqueous solution. Subsequently, a solution of 9-fluorenylmethyl-N-succinimidyl carbonate (4 g, 11.7 mmol) in acetonitrile (40 mL) was slowly added dropwise over a period of 2 hours. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 1 hour. After completion of the reaction, the acetonitrile was removed by distillation under reduced pressure. The aqueous phase was acidified to pH 1 with 10% HCl, at which time a white precipitate was produced. The precipitate was washed sequentially with two portions of 20 mL of water and 20 mL of ethyl acetate, and then dried under reduced pressure to give 4-(fluorenylmethoxycarbonylamino)butanoic acid (Fmoc-GABA) as a white solid in 73% (2.8 g) yield. The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, DMSO-d6, 400 MHz), nuclear magnetic resonance carbon spectroscopy (13C NMR, DMSO-d6, 100 MHz) and mass spectrometry (ESI+).1H NMR (DMSO-d6, 400 MHz): δ 7.89 (d, 2H, J = 7.4 Hz), 7.44 (d, 2H, J = 7.2 Hz), 7.42 (t, 2H, J = 7.5 Hz), 7.35 (s, 1H), 7.33 (t, 2H, J = 7.0 Hz), 4.30 (d, 2H, J = 7 Hz), 4.21 (t, 1H, J = 6.7 Hz), 3.01 (q, 2H, J = 5.6 Hz), 2.20 (t, 2H, J = 7.3 Hz ), 1.63 (q, 2H, J = 7.1 Hz); 13C NMR (DMSO-d6, 100 MHz): δ 142.6, 139.4, 137.4, 128.9, 127.2, 124.2, 121.3, 120.0, 109.6, 77.5, 61.8, 51.1, 31.6; MS (ESI+): m/ z (intensity), 325.8 ([M + H]+, 100%).

References

[1] Chemical Biology and Drug Design, 2015, vol. 86, # 4, p. 837 - 848
[2] Patent: WO2018/144880, 2018, A1. Location in patent: Paragraph 64-65

FMOC-GAMMA-ABU-OH(116821-47-7)Related Product Information

• Fmoc-D-glutamic acid gamma-tert-butyl ester
• FMOC-GLU(OALL)-OH
• Fmoc-L-glutamic acid-gamma-benzyl ester
• FMOC-GAMMA-ABU-OH
• FMOC-GLU(OTBU)-OH H2O
• Fmoc-L-Glutamic acid 1-tert-butyl ester
• FMOC-ABU-OH
• Fmoc-L-beta-homoalanine
• FMOC-GLU(OBZL)-CL
• FMOC-ACHPA
• N-(9-FLUORENYLMETHOXYCARBONYL)-L-GLUTAMIC-15N ACID
• FMOC-GLA(OTBU)2-OH
• FMOC-(3S,4S)-4-AMINO-3-HYDROXY-5-PHENYL PENTANOIC ACID
• FMOC-GLU-OBZL
• FMOC-GLU(OTBU)-OSU
• FMOC-GLU(OTBU)-OPFP
• FMOC-GLU(OTBU)-N-CARBOXYANHYDRIDE
• FMOC-D-GLU-OTBU