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Merck

8.52119

Fmoc-Asn(Dmcp)-OH

Novabiochem®

Synonym(s):

Fmoc-Asn(Dmcp)-OH, N-α-Fmoc-N-β-(1-cyclopropyl-1-methylethyl)-L-asparagine

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About This Item

Empirical Formula (Hill Notation):
C25H28N2O5
CAS Number:
172947-19-2
Molecular Weight:
436.50
MDL number:
MFCD10001340
UNSPSC Code:
12352209
NACRES:
NA.22

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Product Name

Fmoc-Asn(Dmcp)-OH, Novabiochem®

InChI key

XJQSVBZBGZBJDP-NRFANRHFSA-N

SMILES string

N([C@@H](CC(=O)NC(C4CC4)(C)C)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3

product line

Novabiochem®

assay

≥95.0% (acidimetric)
≥98.0% (HPLC)
≥98.0% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

amide

storage temp.

15-25°C

Quality Level

200

Related Categories

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Purity (TLC(CMA2)): ≥ 98.0 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 95.0 %
Water (K. F.): ≤ 2.00 %
Enantiomeric purity: ≥ 99.5 % (a/a)

To see the solvent systems used for TLC of Novabiochem® products please click here.

General description

A superior derivative to Fmoc-Asn(Trt)-OH for the synthesis of Asn-containing peptides by Fmoc SPPS. Fmoc-Asn(Dmcp)-OH is more soluble in DMF than Fmoc-Asn(Trt)-OH, thereby facilitating coupling reactions at higher concentration. Cleavage of the Dmcp group is rapid, even when the residue is located at the N-terminus of a peptide. Coupling of Dmcp-protected derivatives is faster than that of the corresponding hindered Trt derivatives. Dmcp-protected peptides have enhanced solubility.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

[1] L. A. Carpino, et al. (1995) J. Org. Chem., 60, 7718.

Other Notes

Replaces: 04-12-1291

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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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