8.52083

Fmoc-Dpr(ivDde)-OH

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

• 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
• MDL number: MFCD01631659
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Product Name: Fmoc-Dpr(ivDde)-OH, Novabiochem^®
• Quality Segment: 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
• SMILES string: N([C@@H](CNC(=C4C(=O)CC(CC4=O)(C)C)CC(C)C)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3
• 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

Description

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.

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.

Other Notes

Replaces: 04-12-1195

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable