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8.52057

Sigma-Aldrich

Fmoc-Lys(Dde)-OH

Novabiochem®

Synonym(s):
Fmoc-Lys(Dde)-OH, N-α-Fmoc-N-ε-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-L-lysine
Empirical Formula (Hill Notation):
C31H36N2O6
CAS Number:
Molecular Weight:
532.63

Quality Level

product line

Novabiochem®

assay

≥90.0% (acidimetric)
≥97.0% (HPLC)
≥98% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

mp

80 °C (decomposes)

application(s)

peptide synthesis

functional group

amine

storage temp.

15-25°C

General description

Quasi-orthogonally-protected Lys derivative. The Fmoc group can be removed selectively by treatment with piperidine; the Dde group is cleaved with 2% hydrazine in DMF [1]. When removing Dde in the presence of allyl based protecting groups, allyl alcohol should be included in the deprotection solution to prevent reduction of the allyl group [2].

Lys(Dde) has been employed in the following applications: synthesis of branched peptides [1] and di-epitopic peptides [3]; preparation of MAP core molecules and lipo-MAPs [4, 5]; construction of cyclic peptides [6], TASP molecules [7], templates for combinatorial chemistry [8] and synthetic proteins [9]; preparation of peptides modified at the lysine side-chain [10-14].

It has been reported that Dde can migrate from the side-chain of Lys to the unprotected side-chain of another Lys residue [15], and from the β-amino group to the α-amino group of Dpr [16]. In the former instance, this problem can be overcome by using Fmoc-Lys(ivDde)-OH (852082) or using DBU/DMF (2:98) for Fmoc group removal [15, 17].

Full orthogonality of Dde with Fmoc has recently been demonstrated when hydroxylamine is used for Dde removal [18].

The product number for this product was previously 04-12-1121.

To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

Linkage

Replaces: 04-12-1121

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(157B)): ≥ 98 %
Purity (TLC(CMA2)): ≥ 98 %
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 90.0 %
Water (K. F.): ≤ 1.0 %
For TLC-Systems see our General Catalog

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Quality

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