Fmoc-dab(boc)-oh

• CAS: 125238-99-5
• Catalog Number: ACM125238995
• Category: Main Products
• Molecular Weight: 440.49
• Molecular Formula: C₂₄H₂₈N₂O₆
• Synonyms: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid; (S)-4-(Boc-amino)-2-(Fmoc-amino)butyric acid; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)butanoic acid; Fmoc-Dab(Boc)-OH
• IUPAC Name: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoicacid
• Canonical SMILES: CC(C)(C)OC(=O)NCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• InChI Key: LIWKOFAHRLBNMG-FQEVSTJZSA-N
• Boiling Point: 670.9ºC at 760 mmHg
• Flash Point: 359.6ºC
• Density: 1.243g/cm³
• Appearance: white powder
• Exact Mass: 440.19500
• Hazard Statements: Xi
• WGK Germany: 3

Case Study

Fmoc-Dab(Boc)-OH Used in the Synthesis of Polymyxin Mimetic Peptide

Su, Ma, et al. Chemical Communications, 2019, 55(87), 13104-13107.

This work designed several polymyxin derivatives as broad-spectrum antibiotics. Among them, the lead compound P1 can quickly destroy bacterial membranes without developing drug resistance and inhibit the biofilm formed by Escherichia coli. Fmoc-Dab(Boc)-OH can be used in the synthesis process of the polymyxin mimetic peptide lead compound P1.
Synthesis of polymyxin mimic peptide
· Initially, the CTC resin was reacted with Fmoc-Thr(tBu)-OH and DIPEA in DCM solution followed by washing and capping in methanol. The attachment of Fmoc-Dab(Boc)-OH to the resin was achieved by adding Fmoc-Dab(Boc)-OH, DIC, and HOBt in DMF solution, followed by washing.
· Subsequently, the Fmoc protection group was removed using piperidine/DMF solution, and Fmoc-Dab(Boc)-OH was added again. This process was repeated with Fmoc-L-leucine until the desired building blocks were attached.
· After removal of the Fmoc group, palmitic acid was added, followed by removal of the alloc protein group using Pd(PPh3)4 and Me2NH.BH3. The compound was then cleaved using a cocktail of TFE, acetic acid, and DCM. Cyclization was achieved by adding HOBt, TBTU, and DMAP in DCM solvent overnight.
· Finally, the remaining protecting groups were removed using a cocktail of TFA and DCM, and the resulting solution was collected, purified using HPLC, and lyophilized to obtain the pure product compound P1.

Application of Fmoc-Dab(Boc)-OH in the Solid-Phase Synthesis of Polymyxins

Xu, Wei-Liang, et al. Tetrahedron letters, 2015, 56(33), 4796-4799.

A new strategy for the solid-phase synthesis of polymyxins and their analogs that is more convenient and more effective has been developed. The method is to first anchor the amine side chain of Dab9 to the resin and then cyclize it on the resin. Among them, Fmoc-Dab(Boc)-OH is used in the key step of synthesizing moc-Dab(Boc)-OAll.
Synthesis procedure of polymyxin E2
· The Fmoc-Dab(Boc)-OH was reacted with allyl bromide using tricaprylmethylammonium chloride and NaHCO3 to produce Fmoc-Dab(Boc)-OAll, which was then converted to Fmoc-Dab-OAll with a high yield of 81% after removing the Boc group using trifluoroacetic acid (TFA).
· The Fmoc-Dab-OAll was attached to 2CTC resin with N,N-diisopropylethylamine (DIEA) to create compound 1. Next, a linear fully protected peptide 2 was synthesized through solid-phase peptide synthesis (SPPS), using 20% piperidine in DMF for Fmoc deprotection and 1-[Bis(dimethylamino)methylen]-5-chlorobenzotriazolium 3-oxide hexafluorophosphate (HCTU)/DIEA in DMF for coupling.
· After removing the N-(1-(4,4-dimethyl-2,6-dioxocylohexylidene) ethyl (Dde) group with 3% NH2NH2 in DMF, Fmoc-Thr(tBu)-OH was added to the side chain of Dab4 to produce compound 4. The allyl group on Dab9 was then eliminated with Pd(PPh3)4/PhSiH3, followed by Fmoc removal on Thr10.
· The cyclization between Thr10 and Dab9 was achieved using PyAOP with N-methyl morpholine (NMM) and 1-hydroxy-7-azabenzotriazole (HOAt). Finally, the cyclic peptide was released from the 2CTC resin using a cleavage cocktail (TFA/H2O/triisopropylsilane (TIPS) in a ratio of 95/2.5/2.5).

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August 27, 2023

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Custom Q&A

What is the molecular formula of fmoc-dab(boc)-oh?

The molecular formula of fmoc-dab(boc)-oh is C24H28N2O6.

What is the molecular weight of fmoc-dab(boc)-oh?

The molecular weight of fmoc-dab(boc)-oh is 440.5 g/mol.

What are the physical and chemical properties of fmoc-dab(boc)-oh?

Fmoc-dab(boc)-oh is a white or light yellow crystalline solid.

What is the melting point of fmoc-dab(boc)-oh?

The melting point of fmoc-dab(boc)-oh is about 54-56℃.

What is the boiling point of fmoc-dab(boc)-oh?

The boiling point of fmoc-dab(boc)-oh is about 287.8℃.

How is fmoc-dab(boc)-oh extracted or synthesized from natural sources?

Fmoc-dab(boc)-oh is not a naturally occurring compound, it needs to be synthesized by chemical or biological methods.

What is the main application field of fmoc-dab(boc)-oh?

Fmoc-dab(boc)-oh is mainly used as a building block for peptide synthesis, which can be used to synthesize peptides or protein containing L-2,4- diaminobutyric acid residues.

What is security of fmoc-dab(boc)-oh?

Fmoc-dab(boc)-oh is irritating and corrosive, which may cause irritation or damage to skin, eyes, respiratory tract or digestive tract.

What are the precautions of fmoc-dab(boc)-oh?

Wear appropriate protective equipment when using or handling fmoc-dab(boc)-oh, and avoid direct contact or swallowing.

What are the storage conditions of fmoc-dab(boc)-oh?

Fmoc-dab(boc)-oh needs to be stored in a cool and dry place, away from light sources, heat sources and fire sources, and avoid contact with strong oxidants, strong acids, strong bases and other substances.