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Key Documents

8.52072

Sigma-Aldrich

Fmoc-Asp-OAll

Novabiochem®

Synonym(s):

Fmoc-Asp-OAll, N-α-Fmoc-L-aspartic acid α-allyl ester

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About This Item

Empirical Formula (Hill Notation):
C22H21NO6
CAS Number:
144120-53-6
Molecular Weight:
395.41
MDL number:
MFCD00467715
UNSPSC Code:
12352209

Quality Level

200

product line

Novabiochem®

assay

≥97.0% (acidimetric)
≥98% (TLC)
≥98.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

mp

95 °C (decomposes)

application(s)

peptide synthesis

functional group

carboxylic acid

storage temp.

2-30°C

InChI

1S/C22H21NO6/c1-2-11-28-21(26)19(12-20(24)25)23-22(27)29-13-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h2-10,18-19H,1,11-13H2,(H,23,27)(H,24,25)/t19-/m0/s1

InChI key

ZJMVIWUCCRKNHY-IBGZPJMESA-N

Related Categories

General description

Orthogonally-protected building block for the synthesis of head-to-tail cyclic peptides [1,2,3,4,5] by Fmoc SPPS. The α-allyl ester can be selectively removed in the presence of Fmoc- and tBu-based protecting groups by treatment with Pd(Ph3P)4/ CHCl3/AcOH/NMM [6], thereby facilitating the synthesis of branched esters, amides, lactones and lactams incorporating an aspartyl unit.

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

Literature references

[1] W. Bannwarth, et al. (1992) Tetrahedron Lett., 33, 4557.
[2] F. Albericio, et al. (1993) Tetrahedron Lett., 34, 1549.
[3] J. Eichler, et al. (1994) Pept. Res., 7, 300.
[4] J. Eichler, et al. in ′Peptides 1994, Proc. 23rd European Peptide Symposium′, H. Maia (Eds), ESCOM, Leiden, 1994, pp. 461.
[5] J. Eichler, et al. in ′Solid Phase Synthesis & Combinatorial Libraries, 4th International Symposium′, R. Epton (Eds), Mayflower Scientific Ltd., Birmingham, 1996, pp. 201.
[6] S. A. Kates, et al. in ′Peptides, Chemistry, Structure & Biology, Proc. 13th American Peptide Symposium′, ESCOM, Leiden, 1994, pp. 113.

Linkage

Replaces: 04-12-1157

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): conforms
Enantiomeric purity: ≥ 99.0 % (a/a)
Purity (TLC(CMA2)): ≥ 98 %
Purity (TLC(157A)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 97.0 %
Water (K. F.): ≤ 1.5 %

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Articles

Selecting Orthogonal Building Blocks

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications.

Protocols

Selecting Orthogonal Building Blocks

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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