CAS 82911-69-1|2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate|(9H-Fluoren-9-yl)methyl N-succinimidyl carbonate|FMOC-ONSu|1-{[(9H-Fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidine-2,5-dione|2,5-...

General Information

Structure

Molecular Formula

C₁₉H₁₅NO₅

Molecular Mass

337.3261

Exact Mass

337.09502259

Charge

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

Canonic Smiles

O=C(ON1C(=O)CCC1=O)OCC1c2ccccc2c2c1cccc2

Isomeric Smiles

N1(C(=O)CCC1=O)OC(=O)OCC1c2c(cccc2)c2c1cccc2

Calculated Properties

JChem

Acid pKa

17.008211

H Acceptors

H Donor

LogD (pH = 5.5)

2.9514215

LogD (pH = 7.4)

2.9514215

Log P

2.9514215

Molar Refractivity

87.8335

Polarizability

35.36318

Polar Surface Area

72.91

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate

Synonyms

(9H-Fluoren-9-yl)methyl N-succinimidyl carbonateFMOC-ONSu1-{[(9H-Fluoren-9-ylmethoxy)carbonyl]oxy}pyrrolidine-2,5-dioneFmoc-OSu9-芴甲基 N-琥珀酰亚氨基碳酸酯9-Fluorenylmethyl Succinimidyl CarbonateN-(9-芴甲氧羰基氧基)琥珀酰亚胺N-(9-Fluorenylmethoxycarbonyloxy)succinimideFMOC-OSu9-Fluorenylmethyl N-succinimidyl carbonate(2,5-dioxopyrrolidin-1-yl) (9H-fluoren-9-ylmethyl) carbonate9-芴甲基 N-琥珀酰亚胺基碳酸酯N-(9-Fluorenylmethoxycarbonyloxy)succinimideN-(9-Fluorenylmethoxycarbonyloxy)succinimideN-(9-芴基甲氧基羰基)琥珀酰胺1-[[(9H-Fluoren-9-ylmethoxy)carbonyl]oxy]-2,5-pyrrolidinedioneSuccinimidyl (9-Fluorenyl)methyl CarbonateCarbonic Acid 2,5-Dioxo-1-pyrrolidinyl 9H-Fluoren-9-ylmethyl EsterFmoc N-Hydroxysuccinimide EsterN-(9H-Fluoren-9-ylmethoxycarbonyloxy)succinimide(Fluorenylmethoxycarbonyl)hydroxysuccinimide EsterFmoc N-hydroxysuccinimide esterFmoc N-hydroxysuccinimide esterFmoc-OSu9-芴甲基 N-琥珀酰亚胺基碳酸酯

IUPAC name

2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate 2,5-dioxopyrrolidin-1-yl (9H-fluoren-9-yl)methyl carbonate

Names and Identifiers

Registration numbers

PubChem SID

1620431412487057224857201

PubChem CID

CAS Number

EC Number

Beilstein Number

MDL Number

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02199308

White to off-white crystalline powder, purity: ~ 98%
Reagent for the efficient synthesis of FMOC-amino acid, employed as building units in solid phase peptide synthesis.

Sigma Aldrich

289507

Application
Most efficient reagent for the selective preparation of N-(9-fluorenylmethoxycarbonyl) derivatives of hydroxy-amino acids in high yield. Dipeptide formation is lower than with the chloroformate, Fmoc-Cl. It has been employed in the synthesis of glycopeptides.
Packaging
5 g in glass bottle

46920

TRC

F634000

Used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.

Molecule Details

References

PubChem Literature

From Data Sources

• Kothe, U., et al.: Anal. Biochem., 356, 148 (1994)

• Thakkar, A., et al.: Anal. Chem., 78, 5935 (1994)

• Heidenreich, O., et al.: J. Biol. Chem., 269, 2131 (1994)

• Reagent for the preparation of Fmoc derivatives of amino acids, avoiding problems arising from mixed anhydride formation; preferred especially for the protection of hydroxy amino acids: Can. J. Chem., 60, 976 (1982); Biopolymers, 22, 2157 (1983); Synthesis, 671 (1978). For peptide reagents, see Appendix 6.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate

Synonyms

IUPAC name

2,5-dioxopyrrolidin-1-yl 9H-fluoren-9-ylmethyl carbonate 2,5-dioxopyrrolidin-1-yl (9H-fluoren-9-yl)methyl carbonate

Registration numbers

PubChem SID

1620431412487057224857201

PubChem CID

CAS Number

EC Number

Beilstein Number

MDL Number

Molecule Details

White to off-white crystalline powder, purity: ~ 98%
Reagent for the efficient synthesis of FMOC-amino acid, employed as building units in solid phase peptide synthesis.

Sigma Aldrich

289507

46920

TRC

F634000

Used in conjunction with Isothiocyanate to conduct partial Edman Degradation on biologically active peptides.

References

PubChem Literature

From Data Sources

• Kothe, U., et al.: Anal. Biochem., 356, 148 (1994)

• Thakkar, A., et al.: Anal. Chem., 78, 5935 (1994)

• Heidenreich, O., et al.: J. Biol. Chem., 269, 2131 (1994)

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:78372