F9263
N-Fmoc-L-Asparagine (DOD)
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About This Item
Empirical Formula (Hill Notation):
C34H32N2O7
CAS Number:
Molecular Weight:
580.63
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
InChI
1S/C34H32N2O7/c1-41-23-15-11-21(12-16-23)32(22-13-17-24(42-2)18-14-22)36-31(37)19-30(33(38)39)35-34(40)43-20-29-27-9-5-3-7-25(27)26-8-4-6-10-28(26)29/h3-18,29-30,32H,19-20H2,1-2H3,(H,35,40)(H,36,37)(H,38,39)/t30-/m0/s1
SMILES string
COc1ccc(cc1)C(NC(=O)C[C@H](NC(=O)OCC2c3ccccc3-c4ccccc24)C(O)=O)c5ccc(OC)cc5
InChI key
NUINEVHFMAGARJ-PMERELPUSA-N
functional group
Fmoc
storage temp.
−20°C
Application
Fmoc-L-aspartic acid is an N-terminally protected amino acid (Fmoc amino acid) used in solid-phase peptide synthesis (SPPS) to make peptides/glycopeptides containing an the aspartate residue.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Rui Chen et al.
Methods in molecular biology (Clifton, N.J.), 751, 343-355 (2011-06-16)
This chapter describes a rapid and efficient approach for the solid-phase synthesis of N-linked glycopeptides that utilizes on-resin glycosylamine coupling to produce N-linked glycosylation sites. In this method, the full-length nonglycosylated peptide is first synthesized on a solid-phase support using
M Mergler et al.
Journal of peptide science : an official publication of the European Peptide Society, 11(10), 650-657 (2005-04-26)
A newly developed Fmoc-Asp derivative, Fmoc-Asp beta-(2,3,4-trimethyl-pent-3-yl) ester, has been tried in the Fmoc-based SPPS of H-Val-Lys-Asp-Xaa-Tyr-Ile-OH, a well-established peptide model for studying base-catalysed aspartimide formation. When synthesizing the hexapeptide incorporating Gly, Arg(Pbf), Asn(Mtt), Asp(OtBu) or Cys(Acm) for Xaa, considerable
Trent Conroy et al.
Organic & biomolecular chemistry, 8(16), 3723-3733 (2010-06-23)
An efficient strategy for the preparation of N-linked glycopeptides is described. The method relies on the use of side chain protecting groups on aspartic acid residues, namely the allyl and Dmab esters, which are orthogonal to those utilised in Fmoc-strategy
M Mergler et al.
Journal of peptide science : an official publication of the European Peptide Society, 9(8), 518-526 (2003-09-04)
The sequence dependence of base-catalysed aspartmide formation during Fmoc-based SPPS was systematically studied employing the peptide models H-Val-Lys-Asp-Xaa-Tyr-Ile-OH. The extent of formation of aspartimide and related by-products was determined by RP-HPLC. Considerable amounts of by-products were formed in the case
M Mergler et al.
Journal of peptide science : an official publication of the European Peptide Society, 9(1), 36-46 (2003-02-18)
A variety of Asp beta-carboxy protecting groups, Hmb backbone protection and a range of Fmoc cleavage protocols have been employed in syntheses of the model hexapeptide H-VKDGYI-OH to investigate the aspartimide problem in more detail. The extent of formation of
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