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8.52084

Sigma-Aldrich

Fmoc-Dab(ivDde)-OH

Novabiochem®

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Synonym(s):
Fmoc-Dab(ivDde)-OH, N-α-Fmoc-N-γ-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-diaminobutanoic acid
Empirical Formula (Hill Notation):
C32H38N2O6
CAS Number:
Molecular Weight:
546.65

Quality Level

product line

Novabiochem®

Assay

≥95.0% (HPLC)
≥98% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

amine

storage temp.

15-25°C

InChI

1S/C32H38N2O6/c1-19(2)15-26(29-27(35)16-32(3,4)17-28(29)36)33-14-13-25(30(37)38)34-31(39)40-18-24-22-11-7-5-9-20(22)21-10-6-8-12-23(21)24/h5-12,19,24-25,35H,13-18H2,1-4H3,(H,34,39)(H,37,38)/t25-/m0/s1

InChI key

IMMMALLSYWTSAX-VWLOTQADSA-N

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Fmoc-Dab(ivDde)-OH Novabiochem®

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Fmoc-Orn(ivDde)-OH

assay

≥95.0% (HPLC), ≥98% (TLC)

assay

≥95.0% (acidimetric), ≥98% (TLC), ≥99.0% (HPLC)

assay

≥85.0% (acidimetric), ≥97% (TLC), ≥99.0% (HPLC)

assay

≥85.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)

form

powder

form

powder

form

powder

form

powder

functional group

amine

functional group

amine

functional group

amine

functional group

amine

storage temp.

15-25°C

storage temp.

15-25°C

storage temp.

-10 to -25°C

storage temp.

15-25°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

General description

This orthogonally-protected diaminobutyric acid derivative is based on the hindered Dde variant ivDde. The side-chain ivDde group is considerably more stable to piperidine than Dde and is less prone to migrate from protected to unprotected side-chains [1] and from side-chain to γ-amino group [2].When removing ivDde in the presence of allyl-based protecting groups, allyl alcohol should be included in the deprotection solution to prevent reduction of the allyl group [3].

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

Literature references

[1] S. R. Chhabra, et al. (1998) Tetrahedron Lett., 39, 1603.
[2] R. Wilhelm, personal communication.
[3] B. Rohwedder, et al. (1998) Tetrahedron Lett., 39, 1175.
[4] S. K. Sharma, et al. (1999) J. Peptide Res., 53, 501.

Linkage

Replaces: 04-12-1196

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(157A)): ≥ 98 %
Purity (TLC(157B)): ≥ 98 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
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


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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.

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