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46920

Sigma-Aldrich

Fmoc N-hydroxysuccinimide ester

≥98.0% (HPLC)

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/REAXYS Number:
3569540
EC Number:
433-520-5
MDL number:
MFCD00010733
UNSPSC Code:
12352108
PubChem Substance ID:
57650882
NACRES:
NA.22

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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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
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Occupational airborne allergic contact dermatitis from succinimidyl carbonates.
J F Fowler et al.
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International journal of peptide and protein research, 30(3), 431-432 (1987-09-01)
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Monoglucosylated high-mannose-type glycan (Glc1Man9GlcNAc2: G1M9) is well-known as a key glycoform in the glycoprotein folding process, which is specifically recognized by lectin chaperones calnexin (CNX) and calreticulin (CRT) in the endoplasmic reticulum (ER). In this work, we developed an efficient
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