FMOC-STA-OH

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Cat Number

INT158257400

CAS Number

158257-40-0

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Product Detail Description Scientific Support Customer Q&A

CAS Number

158257-40-0

Storage

Under -20℃

Synonyms

FMOC-STATINE;FMOC-LEU-STATINE;FMOC-(3S,4S)-4-AMINO-3-HYDROXY-6-METHYL HEPTANOIC ACID;FMOC-(3S,4S)-STA-OH;(3S,4S)-4-(FMOC-AMINO)-3-HYDROXY-6-METHYLHEPTANOIC ACID

Molecular Formula

C23H27NO5

Molecular Weight

397.46

Smiles

C(O)(=O)C[C@H](O)[C@@H](NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O)CC(C)C

Appearance

White to off-white solid

Melting Point

92-94℃

Boiling Point

628.2℃

Relative Density

1.23

pKa

4.22

General Description

FMOC-STA-OH (Fmoc-Statine) is a gamma-amino-beta-hydroxy acid derivative. Statine is a non-natural amino acid that acts as a transition-state analog for aspartic proteases, making this Fmoc-protected version a powerful tool in drug design.

Mechanism of Action

It acts as a transition-state mimetic. Due to its unique structure, it mimics the tetrahedral intermediate formed during peptide bond hydrolysis, thereby effectively inhibiting the activity of enzymes like pepsin and HIV protease.

Application

It is a critical component in the synthesis of potent protease inhibitors (e.g., Pepstatin analogs) used in the treatment of hypertension, Alzheimer's, and viral infections.

Miraziridine A is a cysteine protease inhibitor isolated from Theonella aff. mirabilis. The synthesis of miraziridine A involves the construction of a key building block, Fmoc-statine (Fmoc-Sta-OH). Starting from (3R,4S)-Boc-statine OEt, an inversion at the C-3 hydroxyl group using methanesulfonyl chloride gives a β-keto ester, followed by hydrolysis and Fmoc protection to yield Fmoc-Sta-OH. This protected statine derivative is then incorporated into a peptide chain assembled on solid support, using Fmoc-Abu-OH and Fmoc-Leu-OH via standard coupling reagents such as DIPC/HOBt. The tetrapeptide is elongated using EtO-Azd-OH with diphenylphosphoryl azide, and the final deprotection is achieved with porcine liver esterase to afford miraziridine A.

Fig. 1 FMOC-STA-OH for the synthesis of miraziridine A. (Alahmdi M. 2018)

References

Alahmdi M. A review of the total synthesis of the most important marine natural products in the Red Se Mohammed Alahmdi. Organic Communications, 2018, 11(1): 1.