| Identification | More | [Name]
N-(9-Fluorenylmethoxycarbonyloxy)succinimide | [CAS]
82911-69-1 | [Synonyms]
1-(9H-FLUORENYLMETHOXYCARBONYLOXY)2,5-PYRROLIDINEDIONE
2,5-PYRROLIDINEDIONE,1-[[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]OXY]-
9-FLUORENMETHYL SUCCINIMIDYL CARBONATE
9-FLUORENYLMETHOXYCARBONYL-N-HYDROXYSUCCINIMIDE
9-FLUORENYLMETHYL N-HYDROXYSUCCINIMIDYL CARBONATE
9-FLUORENYLMETHYL N-SUCCINIMIDYL CARBONATE
9-FLUORENYLMETHYLOXYCARBONYL-N-HYDROXYSUCCINIMIDE
9-FLUORENYLMETHYL SUCCINIMIDYL CARBONATE
CARBONIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTER 9H-FLUOREN-9-YLMETHYL ESTER
CARBONIC ACID FLUORENYLMETHYL SUCCIN-N-YL-ESTER
FLUORENYLMETHYL SUCCINIMIDYL CARBONATE
FMOC N-HYDROXYSUCCINIMIDE ESTER
FMOC-ONSU
FMOC-OSU
FMOC-SU
N-(9-FLUORENEMETHOXYCARBONYLOXY)-SUCCINIMIDE
N-(9-FLUORENYLMETHOXYCARBONYLOXY)SUCCINIMIDE
N-(9-FLUORENYLMETHOXYCARBONYL)SUCCINIMIDE
N-(9-FLUORENYLMETHYLOXYCARBONYLOXY)-SUCCINIMIDE
N-(9H-FLUOREN-2-YLMETHOXYCARBONYLOXY)SUCCINIMIDE | [EINECS(EC#)]
433-520-5 | [Molecular Formula]
C19H15NO5 | [MDL Number]
MFCD00010733 | [Molecular Weight]
337.33 | [MOL File]
82911-69-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [Melting point ]
150-153 °C(lit.)
| [Boiling point ]
150-153°C | [density ]
1.3460 (rough estimate) | [refractive index ]
1.5000 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in dimethyl sulfoxide and dimethyl formamide. | [form ]
Microfine Powder | [color ]
White or almost white | [Sensitive ]
Moisture Sensitive | [Detection Methods]
HPLC(RID),NMR | [BRN ]
3569540 | [Stability:]
Moisture Sensitive | [InChI]
InChI=1S/C19H15NO5/c21-17-9-10-18(22)20(17)25-19(23)24-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2 | [InChIKey]
WMSUFWLPZLCIHP-UHFFFAOYSA-N | [SMILES]
C(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)(=O)ON1C(=O)CCC1=O | [CAS DataBase Reference]
82911-69-1(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
3
| [F ]
10-21 | [Hazard Note ]
Moisture Sensitive | [HazardClass ]
9 | [HS Code ]
29280000 |
| Hazard Information | Back Directory | [Description]
Fmoc-OSu (N-(9-Fluorenylmethoxycarbonyloxy)succinimide) is a reagent used in solid-phase peptide synthesis (SPPS) for Fmoc protection of amino groups, particularly amino acids. This reagent contains an Fmoc functional group, which is stable under acidic conditions and cleaves under alkaline conditions. Fmoc-OSu reacts with amino groups to form stable amide bonds, helping to reduce the occurrence of side reactions. Additionally, Fmoc-OSu can also be used as a fluorescent reagent. | [Chemical Properties]
White powder | [Uses]
N-(9-Fluorenylmethoxycarbonyloxy)succinimide is used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.
| [Uses]
N-protecting reagent for oligonucleotide and peptide syntheses | [Uses]
Reagent for the preparation of pure Fmoc amino acids free from contamination by Fmoc-dipeptides. | [Mechanism of action]
The protective mechanism of Fmoc-OSu involves the amine group (R-NH₂) of the protected molecule acting as a nucleophile and attacking the carbonyl carbon of the Fmoc-OSu molecule, forming a tetrahedral intermediate. where the nitrogen of the amine is now bonded to the carbonyl carbon of the Fmoc group, yielding an Fmoc-protected amine and a succinimide. The Fmoc group is typically removed using bases such as piperidine, which can remove the Fmoc group without hydrolyzing the peptide backbone. In solid-phase peptide synthesis (SPPS), the removal of the Fmoc group occurs via a two-step mechanism: first, the acidic proton at the 9-position of the naphthalene ring system is removed using a mild base (preferably a secondary amine), followed by a β-elimination reaction, generating a highly reactive dibenzofuran (DBF) intermediate, which is immediately captured by the secondary amine to form a stable adduct.
 | [Purification Methods]
Recrystallise the carbonate from CHCl3/Et2O, or from pet ether (b 40-60o). [Pauet Can J Chem 60 976 1982, Lapatsaris et al. Synthesis 671 1983.] |
|
|