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8.52094

Sigma-Aldrich

Fmoc-Lys(Mmt)-OH

≥95.0% (HPLC), for peptide synthesis, Novabiochem®

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Synonym(s):
Fmoc-Lys(Mmt)-OH, N-α-Fmoc-N-ε-4-methoxytrityl-L-lysine
Empirical Formula (Hill Notation):
C41H40N2O5
CAS Number:
159857-60-0
Molecular Weight:
640.77
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

200

product line

Novabiochem®

Assay

≥80.0% (acidimetric)
≥95% (TLC)
≥95.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

amine

storage temp.

2-8°C

InChI

1S/C41H40N2O5/c1-47-32-25-23-31(24-26-32)41(29-14-4-2-5-15-29,30-16-6-3-7-17-30)42-27-13-12-22-38(39(44)45)43-40(46)48-28-37-35-20-10-8-18-33(35)34-19-9-11-21-36(34)37/h2-11,14-21,23-26,37-38,42H,12-13,22,27-28H2,1H3,(H,43,46)(H,44,45)/t38-/m0/s1

InChI key

CTYHQVFFQRDJSN-LHEWISCISA-N

Related Categories

General description

An excellent derivative for the synthesis by Fmoc SPPS of branched peptides and peptides modified at the lysine side-chain [1], and for the construction of templates and multifunctionalized resins for combinatorial synthesis.The side-chain Mmt group can be selectively removed in the same manner as Mtt with 1% TFA in DCM [2,3,4] or DCM/HFIP/TFE/TES (6.5:2:1:0.5) [5]. Alternatively, it can be removed under milder conditions with AcOH/TFE/DCM (1:2:7) [1], leaving Mtt intact.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

[1] S. Matysiak, et al. (1998) Tetrahedron Lett., 39, 1733.
[2] K. Barlos, et al., C. H. Schneider & A. N. Eberle (Eds), ESCOM, Leiden, 1993, pp. 283.
[3] A. Aletras, et al. (1995) Int. J. Peptide Protein Res., 45, 488.
[4] L. Bourel, et al. (2000) J. Peptide Sci., 6, 264.
[5] K. Barlos, personal communication.

Application

  • Synthesis and evaluation of antifungal peptoid derivatives against Cryptococcus neoformans: For drug discovery chemists, this research highlights the use of Fmoc-Lys(Mmt)-OH in synthesizing peptoid derivatives with potential antifungal properties, demonstrating the compound′s utility in developing new antimicrobial agents (M Wassom, 2022).

Linkage

Replaces: 04-12-1232

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(0009)): ≥ 95 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Assay (acidimetric): ≥ 80.0 %
Water (K. F.): ≤ 2.0 %

To see the solvent systems used for TLC of Novabiochem® products please click here.
Product is stabilised with up to 20% diisopropylether upon drying.

Legal Information

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

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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Articles

Selecting Orthogonal Building Blocks

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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