87512-31-0

Basic information

• Product Name: FMOC-ALA-ALA-OH
• Synonyms: Fmoc-L-Ala-L-Ala-OH;(S)-2-((S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)propanamido)propanoic acid;Fmoc-Ala-Ala-OH99%;FMOC-ALA-ALA-OH;FMOC-L-ALANYL-L-ALANINE;FMoc-AA-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-alanyl-L-alanine;FMoc-Ala-Ala
• CAS NO: 87512-31-0
• Molecular Formula: C₂₁H₂₂N₂O₅
• Molecular Weight: 382.41
• Mol File: 87512-31-0.mol

Chemical Properties

• Melting Point: 175-179℃ (ethyl acetate hexane )
• Boiling Point: 674.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.280±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3.49±0.10(Predicted)
• CAS DataBase Reference: FMOC-ALA-ALA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-ALA-ALA-OH(87512-31-0)
• EPA Substance Registry System: FMOC-ALA-ALA-OH(87512-31-0)

Safety Data

• Hazardous Substances Data: 87512-31-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
FMOC-ALA-ALA-OH is utilized as a precursor in solid-phase peptide synthesis for the development of pharmaceuticals. Its role is crucial in creating longer, more complex peptides with precise amino acid sequences, which are essential for the discovery and design of new drugs.
Used in Biochemistry Research:
In the field of biochemistry, FMOC-ALA-ALA-OH is employed as a fundamental component in peptide chemistry. It aids researchers in studying the structure, function, and interactions of peptides, contributing to a deeper understanding of biological processes and the development of bioactive molecules.
Used in Peptide Synthesis:
FMOC-ALA-ALA-OH is used as a protected amino acid building block in the synthesis of custom peptides. Its application ensures that the alanine residues are correctly incorporated into the desired peptide sequence while maintaining the integrity of the peptide during the assembly process.
Used in the Synthesis of Peptide-based Biomaterials:
FMOC-ALA-ALA-OH is used as a component in the synthesis of peptide-based biomaterials, such as hydrogels and scaffolds, for applications in tissue engineering and regenerative medicine. The controlled release of bioactive peptides and the promotion of cell adhesion and proliferation are facilitated by the incorporation of this compound into the biomaterials.
Used in the Development of Diagnostic and Therapeutic Peptides:
FMOC-ALA-ALA-OH is employed in the design and synthesis of diagnostic and therapeutic peptides, including those for imaging, drug delivery, and targeted therapies. Its role in creating specific peptide sequences allows for the development of peptides with tailored properties and functions.

Upstream product

• 1948-31-8 di-L-alanine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 56-41-7 L-alanin 
• 73724-40-0 (S)-2,5-dioxopyrrolidin-1-yl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)propanoate 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 161009-04-7 N-α-(9-fluorenylmethoxycarbonyl)-di-L-alanine tert-butyl ester 
• 93709-88-7 Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanyl-L-alanine methyl ester 
• 86060-86-8 (9H-fluoren-9-yl-methoxy)carbonyl-L-alanine pentafluorophenyl ester 

Downstream Products

• 697805-40-6 C₅₁H₅₈FN₇O₁₀ 
• 1438853-39-4 N^α-Fmoc-Ala-Ala-Asn(N-trityl)-PABC-PNP 

Relevant articles and documents

Alaninyl variants of the marine natural product halocyamine A and their antibacterial properties

In an effort to explore the antibacterial potential of the marine natural product halocyamine A, a series of analogues including desbromo and alanine-substituted variants were synthesised and evaluated for biological activity against a panel of Gram-positive and –negative bacteria. The analogues were synthesised by a combination of solid-phase peptide synthesis and ruthenium complex/ytterbium triflate catalysed hydroamidation chemistry. Single alanine substitutions ([Ala1]-halocyamine A and [Ala2]-halocyamine A) gave only modest increases in activity towards Gram-positive bacteria, while di-alaninyl variants exhibited more potent activity with MIC values of 12.5–50 μM towards the Gram-positive bacteria Staphylococcus aureus and Enterococcus faecalis. A lipophilic trityl-protected intermediate of [Ala2]-halocyamine was the most active against the Gram-negative bacterium Escherichia coli.

Benzoisothiazolone (BIT): A Fast, Efficient, and Recyclable Redox Reagent for Solid Phase Peptide Synthesis

Solid-phase peptide synthesis (SPPS), a preferred synthetic procedure, generates by-products and effluents in multiple equivalents for one equivalent of desired product. Presented herein is the use of a fast and efficient coupling protocol for SPPS using a benzoisothiazolone (BIT), which can be fully recycled. The BIT, as redox activator, works under very mild conditions and generates minimal amount of waste. As a case study, the BIT coupling protocol is applied to the synthesis of side chain of the recently discovered antibiotic, teixobactin.

ANTI-EGFR ANTIBODY DRUG CONJUGATES

The invention relates to anti-Epidermal Growth Factor Receptor (EGFR) antibody drug conjugates (ADCs) which inhibit Bcl-xL, including compositions and methods of using said ADCs.

SPECIFICALLY ACTIVATED MICROMOLECULAR TARGET COUPLING BODY IN TUMOR MICROENVIRONMENT AND USE THEREOF

Provided are an anticancer compound comprising a cleavable linker specifically activated in a tumor microenvironment, and use thereof. The anticancer compound is represented by the following formula, wherein, R1 is a normal functional group or a protection group; R2 is Ala, Thr, Val or Ile; R3 is Ala, Val or Asn; R4 is a drug group linked via a hydroxyl group or an amino group; and the general formula of the drug is R4H. The anticancer compound is only activated at a local portion of a tumor, thus avoiding the defect of immune system damage of a traditional chemotherapeutic drug, and promoting tumor immunization by removing a tumor immunosuppression cell. The anticancer compound or pharmaceutical composition thereof is jointly used with immunotherapy, thus improving the effect of treating the tumor, and effectively inhibiting tumor metastasis and osseous metastasis.

Localized Supramolecular Peptide Self-Assembly Directed by Enzyme-Induced Proton Gradients

Electrodes are ideal substrates for surface localized self-assembly processes. Spatiotemporal control over such processes is generally directed through the release of ions generated by redox reactions occurring specifically at the electrode. The so-used gradients of ions proved their effectiveness over the last decade but are in essence limited to material-based electrodes, considerably reducing the scope of applications. Herein is described a strategy to enzymatically generate proton gradients from non-conductive surfaces. In the presence of oxygen, immobilization of glucose oxidase (GOx) on a multilayer film provides a flow of protons through enzymatic oxidation of glucose by GOx. The confined acidic environment located at the solid–liquid interface allows the self-assembly of Fmoc-AA-OH (Fmoc=fluorenylmethyloxycarbonyl and A=alanine) dipeptides into β-sheet nanofibers exclusively from and near the surface. In the absence of oxygen, a multilayer nanoreactor containing GOx and horseradish peroxidase (HRP) similarly induces Fmoc-AA-OH self-assembly.

ANTI-CD98 ANTIBODIES AND ANTIBODY DRUG CONJUGATES

The invention relates to anti-CD98 antibodies and antibody drug conjugates (ADCs), including compositions and methods of using said antibodies and ADCs.

Maytansinoid derivatives with peptide linker and conjugates thereof

The invention relates to novel cell-binding agent-cytotoxic agent conjugate having a peptide linkers and more specifically to conjugates of formula (I). The invention also provides novel cytotoxic agents of formula (II), linker compounds represented by fo

ANTIBODY DRUG CONJUGATES WITH CELL PERMEABLE BCL-XL INHIBITORS

Small molecule Bcl-xL inhibitors and Antibody Drug Conjugates (ADCs) comprising small molecule Bcl-xL inhibitors are disclosed herein. The Bcl-xL inhibitors and ADCs of the disclosure are useful for, among other things, inhibiting anti-apoptotic Bcl xL proteins as a therapeutic approach towards the treatment of diseases that involve a dysregulated apoptosis pathway.

PEPTIDE-DRUG CONJUGATES

Peptide-drug conjugates comprising p-aminobenzyl carbamoyl or p-aminobenzolyl carbonate self-immolating linkers are disclosed. The peptide-drug conjugates comprise a peptide moiety that can be cleaved by cellular proteases, bound to the self-immolating li

Two-fold odd-even effect in self-assembled nanowires from oligopeptide-polymer-substituted perylene bisimides

Organic nanowires are important building blocks for nanoscopic organic electronic devices. In order to ensure efficient charge transport through such nanowires, it is important to understand in detail the molecular parameters that guide self-assembly of π-conjugated molecules into one-dimensional stacks with optimal constructive π-π overlap. Here, we investigated the subtle relationship between molecular structure and supramolecular arrangement of the chromophores in self-assembled nanowires prepared from perylene bisimides with oligopeptide-polymer side chains. We observed a two-fold odd-even effect in circular dichroism spectra of these derivatives, depending on both the number of l-alanine units in the oligopeptide segments and length of the alkylene spacer between chromophore and oligopeptide substituents. Our results indicate that there is a complex interplay between the translation of molecular chirality into supramolecular helicity and the molecules' inherent propensity for well-defined one-dimensional aggregation into β-sheet-like superstructures in the presence of a central chromophore. Strong excitonic coupling as expressed by the appearance of hypsochromically and bathochromically shifted UV-vis absorptions and strong CD signals was systematically observed for molecules with an odd number of l-alanines in the side chains. The latter derivatives gave rise to nanowires with a significantly higher electron mobility. Our results, hence, provide an important design rule for self-assembled organic nanowires.