Nalpha-FMOC-L-Glutamine Chemical Properties

Melting point:

220 °C (dec.)(lit.)

alpha 

-18 º (c=1,DMF)

Boiling point:

498.73°C (rough estimate)

Density 

1.3116 (rough estimate)

refractive index 

-18 ° (C=1, DMF)

storage temp. 

2-8°C

solubility 

almost transparency in N,N-DMF

form 

powder to crystal

pka

3.73±0.10(Predicted)

color 

White to Almost white

optical activity

[α]20/D 18.5±1.5°, c = 1% in DMF

BRN 

4722773

CAS DataBase Reference

71989-20-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36/37/39-27-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:Fmoc-Gln-OH
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Nalpha-FMOC-L-Glutamine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

N2-Fmoc-L-glutamine is an N-Fmoc-protected form of L-Glutamine (G597000). L-Glutamine is a non-essential amino acid that is important for cells that proliferate quickly in the body, such as those of the immune system. L-Glutamine is known to be especially important for the gut, as it helps to maintain intestinal structure and function. L-Glutamine also has protective properties against host toxicity of chemotherapy in cancer patients.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

To a stirred solution of L-glutamine (1.75 g, 12 mmol) and sodium carbonate (1.27 g, 12 mmol) in 30 mL of water, a solution of 9-fluorenylmethyl-N-succinimidyl carbonate (Fmoc-OSu, 3.0 g, 8.9 mmol) dissolved in 60 mL of tetrahydrofuran (THF) was slowly added. The reaction mixture was stirred overnight at room temperature. Subsequently, THF was removed by distillation under reduced pressure. the residue was diluted with 100 mL of 1N hydrochloric acid and the precipitated white solid was collected by filtration. The solid was further recrystallized in a mixed aqueous solution of DMF with 0.1 N hydrochloric acid to afford the target product (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoic acid as a white powder (2.76 g, 84% yield). The product was characterized by 1H-NMR (90 MHz, DMSO-d6) with chemical shifts of 12.47 (1H, s), 7.89-7.20 (10H, m), 6.68 (1H, s, br), 4.22-3.90 (4H, m), and 2.25-1.86 (4H, m).

References

[1] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[2] Patent: US2006/161007, 2006, A1. Location in patent: Page/Page column 12
[3] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031

Nalpha-FMOC-L-Glutamine(71989-20-3)Related Product Information

• Transglutaminase
• 9-Fluorenylmethyl chloroformate
• Boc-D-Glutamine
• L-Alanyl-L-Glutamine
• L-Glutamine
• Glycyl-L-glutamine monohydrate
• Fmoc-Aib-OH
• Fmoc-OSu
• Fmoc-L-aspartic acid
• Fmoc-D-Asn(Trt)-OH
• FMOC-5-AMINOPENTANOIC ACID
• Fmoc-Gly-OH
• Fmoc-D-phenylalanine
• Fmoc-Met-OH
• FMOC-L-Methionine
• Fmoc-D-leucine
• Fmoc-D-tryptophan
• Fmoc-D-Tyr(tBu)-OH