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8.52083

Sigma-Aldrich

Fmoc-Dpr(ivDde)-OH

≥99.0% (HPLC), for peptide synthesis, Novabiochem®

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Synonym(s):
Fmoc-Dpr(ivDde)-OH, N-α-Fmoc-N-β-1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-3-methylbutyl-L-diaminopropionic acid
Empirical Formula (Hill Notation):
C31H36N2O6
CAS Number:
607366-20-1
Molecular Weight:
532.63
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

200

product line

Novabiochem®

Assay

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

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/C31H36N2O6/c1-18(2)13-24(28-26(34)14-31(3,4)15-27(28)35)32-16-25(29(36)37)33-30(38)39-17-23-21-11-7-5-9-19(21)20-10-6-8-12-22(20)23/h5-12,18,23,25,32H,13-17H2,1-4H3,(H,33,38)(H,36,37)/t25-/m0/s1

InChI key

HLIFXCXTXPXGNH-VWLOTQADSA-N

Related Categories

General description

This orthogonally-protected diaminopropionic 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]. However, migration from side-chain to the unprotected α-amino group of Dpr is unavoidable [2]. This side-reaction can, however, be minimized by the appropriate choice of coupling method for the subsequent residue, see [3].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 [4].

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, et al., Poster 34 presented at the 16th American Peptide Symposium, Minneapolis, 1999.
[3] J. Beythien & P. Schneeberger, in ′Peptides 2000, Proc. 26th European Peptide Symposium′, EDK, Paris, 2001, pp. 361.
[4] B. Rohwedder, et al. (1998) Tetrahedron Lett., 39, 1175.

Linkage

Replaces: 04-12-1195

Analysis Note

Color (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(CMA2)): ≥ 98 %
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 95.0 %
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)

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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Articles

Selecting Orthogonal Building Blocks

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

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