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8.52095

Fmoc-Lys(Mca)-OH

Name: Fmoc-Lys(Mca)-OH
Brand: MM

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

Synonym(s):

Fmoc-Lys(Mca)-OH, N-α-Fmoc-N-ε-7-methoxycoumarin-4-acetyl-L-lysine

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About This Item

Empirical Formula (Hill Notation):

C₃₃H₃₂N₂O₈

CAS Number:

386213-32-7

Molecular Weight:

584.62

MDL number:

MFCD03791024

UNSPSC Code:

12352209

NACRES:

NA.22

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Properties

Product Name

Fmoc-Lys(Mca)-OH, Novabiochem^®

Quality Segment

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.

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.

Other Notes

Replaces: 04-12-1233

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c