| Identification | More | [Name]
Nalpha-FMOC-L-Glutamine | [CAS]
71989-20-3 | [Synonyms]
9-FLUORENYLMETHOXYCARBONYL-L-GLUTAMINE
FMOC-GLN
FMOC-GLN-OH
FMOC-GLUTAMINE
FMOC-L-GLN
FMOC-L-GLN-OH
FMOC-L-GLUTAMINE
N-(9-FLUORENYLMETHOXYCARBONYL)-L-GLUTAMINE
N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMINE
N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-L-GLUTAMINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-GLUTAMINE
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-GLUTAMINE
NALPHA-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-L-GLUTAMINE
N-ALPHA-FMOC-L-GLN
N-ALPHA-FMOC-L-GLUTAMINE
n(alpha)-fluorenylmethoxycarbonylglutamine
N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine
N-α-Fmoc-L-glutamine
NA-FMOC-L-GLUTAMINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-& | [EINECS(EC#)]
276-254-3 | [Molecular Formula]
C20H20N2O5 | [MDL Number]
MFCD00037137 | [Molecular Weight]
368.38 | [MOL File]
71989-20-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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 Rotation]
[α]20/D 18.5±1.5°, c = 1% in DMF | [BRN ]
4722773 | [Major Application]
peptide synthesis | [InChI]
1S/C20H20N2O5/c21-18(23)10-9-17(19(24)25)22-20(26)27-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11H2,(H2,21,23)(H,22,26)(H,24,25)/t17-/m0/s1 | [InChIKey]
IZKGGDFLLNVXNZ-KRWDZBQOSA-N | [SMILES]
NC(=O)CC[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O | [CAS DataBase Reference]
71989-20-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29242990 | [Storage Class]
13 - Non Combustible Solids |
| Hazard Information | Back Directory | [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 |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|