N-Acetyl Semax

An N-terminally acetylated, C-terminally amidated synthetic heptapeptide analog of Semax, retaining the ACTH(4–7) core sequence with a Pro-Gly-Pro C-terminal extension.

Molecular Profile

Type
Synthetic linear heptapeptide derivative (N-terminal acetylation, C-terminal amidation); structural analog of ACTH(4–10)
Molecular formula
C39H54N10O10S
Molecular weight
855.0 g/mol
CAS number
2920938-90-3
Amino acids
7
Sequence
Ac-Met-Glu-His-Phe-Pro-Gly-Pro-NH₂ (acetyl-MEHFPGP-amide)
Modification
N-terminal acetylation and C-terminal amidation of the parent Semax heptapeptide (CAS 80714-61-0); these terminal modifications are the defining structural difference from the parent.

Mechanism & Target Class

N-Acetyl Semax retains the ACTH(4–7) core sequence (Met-Glu-His-Phe) of the parent Semax heptapeptide. The Pro-Gly-Pro C-terminal extension found in the parent confers resistance to carboxypeptidase cleavage. The additional N-terminal acetyl group and C-terminal amide are structural modifications studied for resistance to terminal exopeptidase attack (Shevchenko et al., 2013). Structural chemistry work (Magrì et al., 2016) characterized how N-terminal acetylation alters the copper(II) and zinc(II) coordination geometry of the peptide and examined associated in-vitro properties. Studies of the parent compound used tritium-labeled peptide to characterize specific, reversible, calcium-dependent binding sites in rat basal forebrain membranes. The histidine-containing sequence coordinates Cu(II) and Zn(II) ions, situating it in bioinorganic research contexts.

Storage & Handling

Lyophilized
-20°C, protected from light and moisture; stable long term as lyophilized powder.
Handling
N-terminal acetylation and C-terminal amidation are structural features studied for resistance to terminal exopeptidase cleavage relative to the parent peptide. As with other methionine-containing peptides, protect from oxidizing conditions and avoid repeated freeze-thaw cycles.

Primary Database

PubChem CID 172638603 ↗

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