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8.54000

Sigma-Aldrich

Dde-Lys(Fmoc)-OH

Novabiochem®

Synonym(s):

Dde-Lys(Fmoc)-OH, N-α-1-(4,4-Dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-N-ε-Fmoc-L-lysine

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About This Item

Empirical Formula (Hill Notation):
C31H36N2O6
CAS Number:
156648-40-7
Molecular Weight:
532.63
MDL number:
MFCD00467662
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

200

product line

Novabiochem®

Assay

≥90.0% (acidimetric)
≥96.0% (HPLC)
≥97% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

mp

>70 °C (decomposition)

application(s)

peptide synthesis

functional group

amine

storage temp.

15-25°C

SMILES string

N([C@@H](CCCCNC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O)C(=C1C(=O)CC(CC1=O)(C)C)C

InChI

1S/C31H36N2O6/c1-19(28-26(34)16-31(2,3)17-27(28)35)33-25(29(36)37)14-8-9-15-32-30(38)39-18-24-22-12-6-4-10-20(22)21-11-5-7-13-23(21)24/h4-7,10-13,24-25,33H,8-9,14-18H2,1-3H3,(H,32,38)(H,36,37)/t25-/m0/s1

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]. Also available Fmoc-Lys(Dde)-OH 852057. This derivative has been employed in Fmoc SPPS to facilitate the introduction of biotin to the side-chain of lysine [3].

Associated Protocols and Technical Articles
Guide to Selection of Orthogonally-Protected Building Blocks for Fmoc SPPS

Literature references

[1] B. W. Bycroft, et al. (1993) J. Chem. Soc., Chem. Commun., 778.
[2] B. Rohwedder, et al. (1998) Tetrahedron Lett., 39, 1175.
[3] J. Mack, et al. (1999) Lett. Pept. Sci., 6, 135.

Linkage

Replaces: 04-12-5201

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)): ≥ 97 %
Purity (TLC(CMA2)): ≥ 97 %
Assay (HPLC, area%): ≥ 96.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 90.0 %
Water (K. F.): ≤ 1.00 %

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

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

Certificates of Analysis (COA)

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Articles

Selecting Orthogonal Building Blocks

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications.

Protocols

Selecting Orthogonal Building Blocks

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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