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Sigma-Aldrich

Fmoc N-hydroxysuccinimide ester

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

9-Fluorenylmethyl N-succinimidyl carbonate, N-(9-Fluorenylmethoxycarbonyloxy)succinimide, Fmoc-OSu

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About This Item

Empirical Formula (Hill Notation):
C19H15NO5
CAS Number:
82911-69-1
Molecular Weight:
337.33
Beilstein:
3569540
EC Number:
433-520-5
MDL number:
MFCD00010733
UNSPSC Code:
12352108
PubChem Substance ID:
57650882
NACRES:
NA.22

product name

Fmoc N-hydroxysuccinimide ester, ≥98.0% (HPLC)

Quality Level

200

Assay

≥98.0% (HPLC)

form

powder

mp

150-153 °C (lit.)

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

O=C(OCC1c2ccccc2-c3ccccc13)ON4C(=O)CCC4=O

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

InChI key

WMSUFWLPZLCIHP-UHFFFAOYSA-N

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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.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302 - H317 - H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A. Paquet
Canadian Journal of Chemistry, 60, 976-976 (1982)
Occupational airborne allergic contact dermatitis from succinimidyl carbonates.
J F Fowler et al.
Contact dermatitis, 45(1), 38-38 (2001-06-26)
Improved purities for Fmoc-amino acids from Fmoc-ONSu.
R C Milton et al.
International journal of peptide and protein research, 30(3), 431-432 (1987-09-01)
Huaimin Wang et al.
Scientific reports, 5, 16680-16680 (2015-11-18)
Biocompatible peptide-based supramolecular hydrogel has recently emerged as a new and promising system for biomedical applications. In this work, Rhodamine B is employed as a new capping group of self-assembling peptide, which not only provides the driving force for supramolecular
Stancho Stanchev et al.
Journal of peptide science : an official publication of the European Peptide Society, 20(9), 725-735 (2014-06-13)
The antimicrobial 40-amino-acid-peptide lucifensin was synthesized by native chemical ligation (NCL) using N-acylbenzimidazolinone (Nbz) as a linker group. NCL is a method in which a peptide bond between two discreet peptide chains is created. This method has been applied to
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