F4061
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:
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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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
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.
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