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Merck
CN
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安全信息

F4061

Sigma-Aldrich

Fmoc-Lys(Mca)-OH

别名:

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

经验公式(希尔记法):
C33H32N2O8
分子量:
584.62
UNSPSC代码:
12352200
NACRES:
NA.26

反应适用性

reaction type: Fmoc solid-phase peptide synthesis

应用

peptide synthesis

官能团

Fmoc

储存温度

−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

应用

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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说明
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WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

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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)
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
Fluorescent labeling of peptides on solid phase
Katritzky AR, et al.
Organic & Biomolecular Chemistry, 6(24), 4582-4586 (2008)

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