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8.52079

Fmoc-Asp-ODmab

Novabiochem®

Synonym(s):

Fmoc-Asp-ODmab, N-α-Fmoc-L-aspartic acid α-4-{N-[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]-amino} benzyl ester

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About This Item

Empirical Formula (Hill Notation):
C39H42N2O8
CAS Number:
172611-77-7
Molecular Weight:
666.76
MDL number:
MFCD00797876
UNSPSC Code:
12352209
NACRES:
NA.22
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Quality Segment

200

product line

Novabiochem®

assay

≥95.0% (HPLC), ≥97% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

carboxylic acid

storage temp.

15-25°C

SMILES string

N([C@@H](CC(=O)O)C(=O)OCc4ccc(cc4)NC(=C5C(=O)CC(CC5=O)(C)C)CC(C)C)C(=O)OCC1c2c(cccc2)c3c1cccc3

InChI

1S/C39H42N2O8/c1-23(2)17-31(36-33(42)19-39(3,4)20-34(36)43)40-25-15-13-24(14-16-25)21-48-37(46)32(18-35(44)45)41-38(47)49-22-30-28-11-7-5-9-26(28)27-10-6-8-12-29(27)30/h5-16,23,30,32,40H,17-22H2,1-4H3,(H,41,47)(H,44,45)/t32-/m0/s1

InChI key

QPTKEHUFSCXXEH-YTTGMZPUSA-N

General description

Quasi-orthogonally-protected Asp derivative.The Dmab group can be removed selectively in the presence of tBu-based protecting groups by treatment with 2% hydrazine in DMF [1], making this derivative an extremely useful tool for the preparation of cyclic peptides by Fmoc SPPS or for library synthesis. Occasionally sluggish cleavage of the aminobenzyl moiety is observed [2,3]. In these instances, washing the support with 20% DIPEA in DMF/water (9:1) [2] or HCl in dioxane [4] has been found to be efficacious. For the on-resin synthesis of side-chain to side-chain lactam bridged peptides, the combination of Lys(ivDde) and Asp(ODmab) is particularly advantageous since both side-chains can be simultaneously unmasked in a single step.To avoid aspartimide formation, it is advisable to employ an Hmb- or Dmb-protected derivative for introduction of the preceding residue.For applications of this derivative in the synthesis of cyclic peptides, see references [5 - 7].

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

Literature references

[1] W. C. Chan, et al. (1995) J. Chem. Soc., Chem. Commun., 2209.
[2] S. Künzel, et al. Poster 17 presented at Solid Phase Synthesis & Combinatorial Libraries, Southampton, September 2001.
[3] K. F. Medzihradszky, et al. (2002) Lett. Pept. Sci., 8, 1.
[4] Albericio, et al.Poster 44 presented at American Peptide Symposium, San Diego 2005..
[5] M. Cudic, et al. in ′Peptides 2000, Proc. 26th European Peptide Symposium′, J. Martinez & J.-A. Fehrentz (Eds), Paris, Editions EDK, 2001, pp. 203.
[6] M. Cudic, et al. (2000) Tetrahedron Lett., 41, 4527.
[7] J. P. Malkinson, et al. (2003) Org. Lett., 5, 5051.

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.0 % (a/a)
Purity (TLC(157A)): ≥ 97 %
Purity (TLC(CMA2)): ≥ 97 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Water (K. F.): ≤ 1.0 %

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

Other Notes

Replaces: 04-12-1176

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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