8.52095

Fmoc-Lys(Mca)-OH

≥97.0% (HPLC), for peptide synthesis, Novabiochem^®

• Synonym(s): Fmoc-Lys(Mca)-OH, N-α-Fmoc-N-ε-7-methoxycoumarin-4-acetyl-L-lysine
• Empirical Formula (Hill Notation): C₃₃H₃₂N₂O₈
• CAS Number: 386213-32-7
• Molecular Weight: 584.62
• MDL number: MFCD03791024
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Product Name: Fmoc-Lys(Mca)-OH, Novabiochem^®
• Quality Level: 200
• product line: Novabiochem^®
• Assay: ≥97% (TLC); ≥97.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: amine
• storage temp.: −20°C
• SMILES string: N([C@@H](CCCCNC(=O)Cc4c5c([o][c](c4)=O)cc(cc5)OC)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3
• InChI: 1S/C33H32N2O8/c1-41-21-13-14-22-20(17-31(37)43-29(22)18-21)16-30(36)34-15-7-6-12-28(32(38)39)35-33(40)42-19-27-25-10-4-2-8-23(25)24-9-3-5-11-26(24)27/h2-5,8-11,13-14,17-18,27-28H,6-7,12,15-16,19H2,1H3,(H,34,36)(H,35,40)(H,38,39)/t28-/m0/s1
• InChI key: BWJJONDPLYEAMC-NDEPHWFRSA-N

Description

General description

A modified lysine derivative for the preparation of fluorogenically-labeled peptides by Fmoc SPPS ^[1]. The Mca group fluoresces at 405 nm when stimulated at 340 nm, and is most commonly used in conjunction with Dabcyl and 2,4-dinitrophenyl quenching groups. Recently, Fmoc-Lys(Mca)-OH has been used to prepare lanthanide-based luminescent proteins by native chemical ligation ^[2]. Lys(Mca) was found to be stable to HF cleavage conditions used to synthesize the thioester fragments needed for ligation.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Chromogenic Labeling of Synthetic Peptides

Literature references

^[1] J. L. Lauer-Fields, et al. (2001) Biochemistry, 40, 5795.
^[2] C. F. W. Becker, et al. (2004) Bioconjugate Chem., 15, 1118.

Linkage

Replaces: 04-12-1233

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 %
Assay (HPLC, area%): ≥ 97.0 % (a/a)
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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable