8.52086

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
• Empirical Formula (Hill Notation): C₂₈H₂₇NO₆
• CAS Number: 200336-86-3
• Molecular Weight: 473.52
• MDL number: MFCD00237012
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Product Name: Fmoc-Asp(O-2-PhiPr)-OH, Novabiochem^®
• Quality Segment: 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
• SMILES string: N([C@@H](CC(=O)OC(C)(C)c4ccccc4)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3
• 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

Description

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.

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.

Other Notes

Replaces: 04-12-1200

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable