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8.52086

Sigma-Aldrich

Fmoc-Asp(O-2-PhiPr)-OH

≥97% (TLC), for peptide synthesis, Novabiochem®

Synonym(s):

Fmoc-Asp(O-2-PhiPr)-OH, N-α-Fmoc-L-aspartic acid β-2-phenylisopropyl ester

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About This Item

Empirical Formula (Hill Notation):
C28H27NO6
CAS Number:
200336-86-3
Molecular Weight:
473.52
UNSPSC Code:
12352209
NACRES:
NA.22

product name

Fmoc-Asp(O-2-PhiPr)-OH, Novabiochem®

Quality Level

200

product line

Novabiochem®

Assay

≥93.0% (acidimetric)
≥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

Fmoc

storage temp.

15-25°C

InChI

1S/C28H27NO6/c1-28(2,18-10-4-3-5-11-18)35-25(30)16-24(26(31)32)29-27(33)34-17-23-21-14-8-6-12-19(21)20-13-7-9-15-22(20)23/h3-15,23-24H,16-17H2,1-2H3,(H,29,33)(H,31,32)/t24-/m0/s1

InChI key

MEAHCBOPNIDLFH-DEOSSOPVSA-N

General description

Quasi-orthogonally-protected Asp derivative.The 2-PhiPr group can be removed selectively in the presence of tBu-based protecting groups by treatment with 1% TFA in DCM [1], making this derivative an extremely useful tool for the preparation of cyclic peptides by Fmoc SPPS [2] or for library synthesis. For the on-resin synthesis of side-chain to side-chain lactam bridged peptides, the combination of Lys(Mtt) and Asp(O-2-PhiPr) is particularly advantageous since both side-chains can be simultaneously unmasked in a single step.This derivative has also been used in solution to prepare bicyclic helix initiating peptides [3].

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

Literature references

[1] C. Yue, et al. (1993) Tetrahedron Lett., 34, 323.
[2] F. Dick, et al. in ′Peptides 1996, Proc. of 24th European Peptide Symposium′, R. Ramage & R. Epton (Eds), Mayflower Scientific Ltd., Birmingham, 1998, pp. 339.
[3] J. W. Taylor, et al., Poster 185 presented at the American Peptide Symposium, San Diego, 2001.

Linkage

Replaces: 04-12-1200

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(011A)): ≥ 97 %
Purity (TLC(0811)): ≥ 97 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 93.0 %
Water (K. F.): ≤ 2.0 %

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 Code

11 - Combustible Solids

WGK

WGK 2

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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