Ac-Lys(Fmoc)-OH

Ac-Lys(Fmoc)-OH is an N-acetylated lysine derivative bearing an Fmoc-protecting group on the side-chain amino functionality, with a free α-amino and α-carboxyl group characteristic of an amino acid building block. The ε-amino group is masked by the Fmoc carbamate to control chemoselectivity during peptide assembly, while the N-acetyl (Ac-) modification differentiates the α-amino reactivity from the protected side chain. In synthesis, this protected lysine analogue is used as a precursor for stepwise peptide construction and for preparing lysine-containing peptide derivatives where selective functional group handling and controlled incorporation of the lysine side chain are required.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Ac-Lys(Fmoc)-OH(CAS 148101-51-3)

CAT No: CP26405

CAS No:148101-51-3

Synonyms/Alias:Ac-Lys(Fmoc)-OH;148101-51-3;L-Lysine, N2-acetyl-N6-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2S)-2-acetamido-6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid;MFCD08458546;SCHEMBL15669665;N2-acetyl-N6-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-lysine;HPXGLFPXINBZFY-NRFANRHFSA-N;AKOS025289345;DS-9736;CS-0154010;F10646;EN300-1716612;S-148101-51-3;(2S)-2-acetamido-6-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid;(2S)-2-ACETAMIDO-6-{[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO}HEXANOIC ACID;

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cGMP Peptide
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  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C23H26N2O5
M.W/Mr.
410.5
Sequence
Three Letter Code:Ac-Lys(Fmoc)(Fmoc)-OH

Ac-Lys(Fmoc)-OH is an N-acetylated, Fmoc-protected lysine derivative used as a protected amino acid building block for peptide assembly. The lysine side chain retains the protected ε-amino functionality characteristic of Fmoc-based workflows, while the N-acetyl (Ac-) group provides an additional terminal protection strategy that helps define peptide N-terminus chemistry during synthesis and downstream handling. This reagent is commonly selected when a controlled lysine residue with an Fmoc-enabled coupling site is required for constructing protected peptide intermediates and defined peptide sequences.

1. Fmoc Peptide Building Block

Ac-Lys(Fmoc)-OH is used by peptide synthesis groups to incorporate a lysine residue into Fmoc-based peptide sequences while maintaining an N-acetylated N-terminus. Custom peptide manufacturers and academic peptide chemistry labs rely on this type of protected lysine derivative to build peptide intermediates where the N-terminus must remain capped through iterative coupling steps. The Fmoc functionality supports standard solid-phase or solution-phase coupling workflows, and the lysine side-chain functionality supports the generation of peptides that require lysine-containing motifs for subsequent functionalization or biological study.

2. Defined N-Terminus Peptide Synthesis

Ac-Lys(Fmoc)-OH supports workflows that require explicit control of N-terminal capping, particularly when the target peptide design calls for an acetylated amino terminus. Protein engineering teams and chemical biology researchers often use such capped lysine building blocks to generate peptides that mimic specific post-translational or chemically defined N-terminus states for structure-function studies. By using a pre-acetylated lysine building block, developers can reduce variability in N-terminus chemistry across peptide libraries and improve reproducibility when comparing peptides that differ at lysine position(s) or surrounding sequence context.

3. Peptide Library and SAR Intermediates

Ac-Lys(Fmoc)-OH is frequently incorporated into peptide library synthesis and medicinal chemistry intermediate preparation where lysine-containing analogs are required for SAR (structure-activity relationship) studies. Medicinal chemistry groups use Fmoc-protected lysine derivatives to rapidly generate series of protected peptide fragments that can be further elaborated into conjugates, cyclized motifs, or larger constructs. The reagent's protected amino acid format helps streamline downstream purification and handling of intermediate peptides by maintaining orthogonal protection patterns typical of Fmoc-based synthetic pipelines.

4. Lysine-Containing Conjugation Precursors

Ac-Lys(Fmoc)-OH is also used to prepare lysine-containing peptide precursors intended for later derivatization steps in bioconjugation workflows. Chemical biology laboratories often start from defined, protected peptide intermediates that include lysine residues as handles for subsequent conjugation chemistry, enabling the construction of peptide-based probes, affinity reagents, or labeled biomolecular tools. The combination of controlled N-terminal protection and Fmoc-enabled peptide assembly makes Ac-Lys(Fmoc)-OH a practical starting material when the downstream conjugation strategy depends on having a lysine-bearing peptide scaffold with consistent sequence and terminal capping.

Size
1 g;5 g;
InChI
InChI=1S/C23H26N2O5/c1-15(26)25-21(22(27)28)12-6-7-13-24-23(29)30-14-20-18-10-4-2-8-16(18)17-9-3-5-11-19(17)20/h2-5,8-11,20-21H,6-7,12-14H2,1H3,(H,24,29)(H,25,26)(H,27,28)/t21-/m0/s1
InChI Key
HPXGLFPXINBZFY-NRFANRHFSA-N
Canonical SMILES
CC(=O)NC(CCCCNC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O

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