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Merck
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Principaux documents

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F9263

Sigma-Aldrich

N-Fmoc-L-Asparagine (DOD)

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About This Item

Formule empirique (notation de Hill):
C34H32N2O7
Numéro CAS:
119062-05-4
Poids moléculaire :
580.63
Numéro MDL:
MFCD00065623
Code UNSPSC :
12352200
ID de substance PubChem :
24894994

Groupe fonctionnel

Fmoc

Température de stockage

−20°C

Chaîne SMILES 

COc1ccc(cc1)C(NC(=O)C[C@H](NC(=O)OCC2c3ccccc3-c4ccccc24)C(O)=O)c5ccc(OC)cc5

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

Clé InChI

NUINEVHFMAGARJ-PMERELPUSA-N

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Benjamin M Swarts et al.
Carbohydrate research, 343(17), 2894-2902 (2008-09-16)
The syntheses of five natural and N-terminal acetylated peptides and glycopeptides of the CD52 antigen are described. Solid phase peptide synthesis was employed in the construction of the target compounds from Fmoc-protected commercial amino acids and synthetic glycan-asparagine conjugates. Circular
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
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, 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
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
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