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F4061

Sigma-Aldrich

Fmoc-Lys(Mca)-OH

Synonym(s):

N-α-Fmoc-N-ε-7-methoxycoumarin-4-acetyl-L-Lys-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
UNSPSC Code:
12352200
NACRES:
NA.26

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

−20°C

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

Application

Fmoc-Lys(Mca)-OH can be used as a building block to prepare fluorescent labeled peptides by solid-phase peptide synthesis. It is also used to synthesize luminescent lanthanide(III)-based chelates for spectroscopic applications, in particular, to label folded proteins or DNA.

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Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Fluorescent labeling of peptides on solid phase
Katritzky AR, et al.
Organic & Biomolecular Chemistry, 6(24), 4582-4586 (2008)
Christian F W Becker et al.
Bioconjugate chemistry, 15(5), 1118-1124 (2004-09-16)
A synthesis strategy for the on-resin assembly of luminescent lanthanide chelates from commercially available compounds was developed. Advantages of the approach include the absence of spacers between the metal ion and the attachment site, and the compatibility with typical chemical
Alan R Katritzky et al.
Organic & biomolecular chemistry, 6(24), 4582-4586 (2008-11-29)
N(alpha)-Fmoc-N(epsilon)-[(7-methoxycoumarin-4-yl)acetyl]-L-lysine (N(alpha)-Fmoc-L-Lys(Mca)-OH) 3 is conveniently prepared by benzotriazole methodology (52% over two steps). N-Acylbenzotriazoles Mca-Bt 2, N(alpha)-Fmoc-L-Lys(Mca)-Bt 4, coumarin-3-ylcarbonyl (Cc)-Bt 5, N(alpha)-Fmoc-L-Lys(Cc)-Bt 7 and N(alpha)-(Cc)-L-Lys(Fmoc)-Bt 9 enable the efficient microwave enhanced solid-phase fluorescent labeling of peptides.
On-resin assembly of a linkerless lanthanide (III)-based luminescence label and its application to the total synthesis of site-specifically labeled mechanosensitive channels
Becker C FW, et al.
Bioconjugate Chemistry, 15(5), 1118-1124 (2004)

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