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8.52094

Sigma-Aldrich

Fmoc-Lys(Mmt)-OH

Novabiochem®

Synonym(s):

Fmoc-Lys(Mmt)-OH, N-α-Fmoc-N-ε-4-methoxytrityl-L-lysine

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About This Item

Empirical Formula (Hill Notation):
C41H40N2O5
CAS Number:
Molecular Weight:
640.77
UNSPSC Code:
12352209

Quality Level

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

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

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications.

Protocols

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications

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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