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8.52120

Fmoc-Gln(Dmcp)-OH

Novabiochem®

Synonym(s):

Fmoc-Gln(Dmcp)-OH, N-α-Fmoc-N-γ-(1-cyclopropyl-1-methylethyl)-L-glutamine

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About This Item

Empirical Formula (Hill Notation):
C26H30N2O5
CAS Number:
172947-20-5
Molecular Weight:
450.53
MDL number:
MFCD10001341
UNSPSC Code:
12352209
NACRES:
NA.22
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Quality Segment

200

product line

Novabiochem®

assay

≥90.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)

form

solid

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

amide

storage temp.

15-25°C

SMILES string

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

InChI

1S/C26H30N2O5/c1-26(2,16-11-12-16)28-23(29)14-13-22(24(30)31)27-25(32)33-15-21-19-9-5-3-7-17(19)18-8-4-6-10-20(18)21/h3-10,16,21-22H,11-15H2,1-2H3,(H,27,32)(H,28,29)(H,30,31)/t22-/m0/s1

InChI key

JHXHPPOYVOMYCD-QFIPXVFZSA-N

General description

A superior derivative to Fmoc-Gln(Trt)-OH for the synthesis of Gln-containing peptides by Fmoc SPPS. Fmoc-Gln(Dmcp)-OH is more soluble in DMF than Fmoc-Gln(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.

Analysis Note

Assay (acidimetric): ≥ 90.0 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Water (K. F.): ≤ 1.00 %
Identity (IR): passes test
Solubility (1 mmole in 2 ml DMF): passes test
Color (visual): passes test
Appearance of substance (visual): passes test
Purity (TLC(CMA2)): ≥ 98 %
Enantiomeric purity: ≥ 99.5 % (a/a)

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

Other Notes

Replaces: 04-12-1292

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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