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47624

Sigma-Aldrich

Fmoc-Lys(Boc)-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

Nα-Fmoc-Nε-Boc-L-lysine

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About This Item

Empirical Formula (Hill Notation):
C26H32N2O6
CAS Number:
71989-26-9
Molecular Weight:
468.54
Beilstein:
4217767
EC Number:
276-256-4
MDL number:
MFCD00037138
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57651044
NACRES:
NA.26

product name

Fmoc-Lys(Boc)-OH, ≥98.0% (HPLC)

Assay

≥98.0% (HPLC)

form

solid

optical activity

[α]20/D −12±1°, c = 1% in DMF

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Boc
Fmoc

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

InChI

1S/C26H32N2O6/c1-26(2,3)34-24(31)27-15-9-8-14-22(23(29)30)28-25(32)33-16-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h4-7,10-13,21-22H,8-9,14-16H2,1-3H3,(H,27,31)(H,28,32)(H,29,30)/t22-/m0/s1

InChI key

UMRUUWFGLGNQLI-QFIPXVFZSA-N

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General description

Fmoc-Lys(Boc)-OH is an amino acid derivative used as a reagent in Fmoc solid-phase peptide synthesis.

Application

Fmoc-Lys(Boc)-OH can be used for:
  • The solid-phase synthesis of pentasubstituted dihydroimidazolylbutyl dihydroimidazol-3-ium salts by coupling with p-methylbenzhydrylamine (MBHA) resin.
  • Fmoc-based peptide synthesis of bis-naphthalene diimide, a threading intercalator.
  • Synthesis of ε-Boc-ε-(3,5-bis-trifluoromethyl-benzyl)-α-Fmoc-L-Lysine to be used as 19F NMR based screening tool.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Marine Bacchi et al.
Protein science : a publication of the Protein Society, 25(12), 2225-2242 (2016-09-28)
Synthetic biology (or chemical biology) is a growing field to which the chemical synthesis of proteins, particularly enzymes, makes a fundamental contribution. However, the chemical synthesis of catalytically active proteins (enzymes) remains poorly documented because it is difficult to obtain
Marta Kulik et al.
Biochimie, 138, 32-42 (2017-04-12)
A fragment of 23S ribosomal RNA (nucleotides 1906-1924 in E. coli), termed Helix 69, forms a hairpin that is essential for ribosome function. Helix 69 forms a conformationally flexible inter-subunit connection with helix 44 of 16S ribosomal RNA, and the nucleotide
Improved synthesis of polyfluorinated l-lysine for 19F NMR-based screening.
Malgesini B, et al.
Molecular Diversity, 13(1), 53-56 (2009)
Solid-phase parallel synthesis of substituted dihydroimidazolylbutyl dihydroimidazol-3-ium salts.
Acharya AN, et al.
Tetrahedron Letters, 43(7), 1157-1160 (2002)
Kavita Bansal et al.
Bioconjugate chemistry, 29(4), 1102-1110 (2018-03-01)
Peptide-based drug delivery systems have become a mainstay in the contemporary medicinal field, resulting in the design and development of better pharmaceutical formulations. However, most of the available reports employ tedious multiple reaction steps for the conjugation of bioactive cationic
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