94744-50-0

Basic information

• Product Name: Fmoc-Aib-OH
• Synonyms: N-FMOC-C-ALPHA-METHYLALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-ALPHA-METHYL-L-ALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-ALPHA-AMINOISOBUTYRIC ACID;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-AMINOISOBUTYRIC ACID;N-ALPHA-FMOC-ALPHA-AMINOISOBUTYRIC ACID;N-ALPHA-FMOC-L-ALPHA-AMINOISOBUTYRIC ACID;RARECHEM EM WB 0053;FMOC-AIB-OH
• CAS NO: 94744-50-0
• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.36
• EINECS: 2017-001-1
• Product Categories: Amino Acids;Unusual Amino Acids;Amino Acids 13C, 2H, 15N;Amino Acid Derivatives;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;peptides
• Mol File: 94744-50-0.mol

Chemical Properties

• Melting Point: 182-188 °C
• Boiling Point: 544.3 °C at 760 mmHg
• Flash Point: 283 °C
• Appearance: /
• Density: 1.256 g/cm³
• Refractive Index: 1.614
• Storage Temp.: 2-8°C
• PKA: 3.98±0.10(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 5604328
• CAS DataBase Reference: Fmoc-Aib-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-Aib-OH(94744-50-0)
• EPA Substance Registry System: Fmoc-Aib-OH(94744-50-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• HazardClass: IRRITANT
• Hazardous Substances Data: 94744-50-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Fmoc-Aib-OH is used as a building block in chemical synthesis for the creation of complex organic molecules and compounds. Its unique structure allows for the formation of stable bonds and the development of novel chemical entities.
Used in Peptide Chemistry:
In peptide chemistry, Fmoc-Aib-OH is used as an amino acid derivative to facilitate the synthesis of peptides and proteins. Its presence in peptide sequences can influence the overall structure, stability, and function of the resulting polypeptides.
Used in Encoded Amino Acid Scanning:
Fmoc-Aib-OH is used for studying receptor-ligand interactions using encoded amino acid scanning. This technique allows researchers to gain insights into the binding properties and mechanisms of various molecules, leading to the development of more effective drugs and therapeutic agents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Fmoc-Aib-OH is used as a key component in the development of new drugs and therapeutic agents. Its unique properties and versatility make it an essential tool in the design and synthesis of novel pharmaceutical compounds.
Used in Research and Development:
Fmoc-Aib-OH is also used in research and development settings to explore new applications and properties of this alanine derivative. Its potential uses in various fields, such as materials science, nanotechnology, and biotechnology, are being investigated to unlock its full potential.

InChI:InChI=1/C19H19NO4/c1-19(20,18(22)23)10-17(21)24-11-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,16H,10-11,20H2,1H3,(H,22,23)

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 5938-34-1 2-amino-2-methyl-propanoic acid hydrochloride 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 1072922-73-6 C₁₄H₁₅NO₂ 
• 150458-42-7 (9H-fluoren-9-yl)methyl 1-fluoro-2-methyl-1-oxopropan-2-ylcarbamate 
• 62-57-7 2-Aminoisobutyric acid 

Downstream Products

• 394208-20-9 C₂₁H₃₈N₄O₇ 
• 1377686-95-7 C₂₅H₄₅N₅O₈ 
• 79638-64-5 N-tert-butoxycarbonyl α,α-dimethylglycyl α,α-dimethylglycine 
• 663604-50-0 N-tert-butoxycarbonyl α,α-dimethylglycyl α,α-dimethylglycyl α,α-dimethylglycine 
• 95852-71-4 H-Tyr-Aib-Aib-Phe-Leu-NH₂ 
• 95852-51-0 Aib-Phe-Leu-NH₂ 
• 1196043-39-6 CbzNH-L-His-Gly-L-His-D-Pro-Aib-L-His-Gly-L-His-NH₂ 
• 1196043-47-6 CbzNH-L-His-Gly-L-Ser-D-Pro-Aib-L-Ser-Gly-L-His-NH₂ 
• 1196043-45-4 CbzNH-L-His-Gly-L-Ser-D-Pro-Aib-L-His-Gly-L-Ser-NH₂ 
• 1196043-40-9 CbzNH-L-His-Gly-L-His-D-Pro-Aib-L-His-Gly-L-Ser-NH₂ 
• 1196043-48-7 CbzNH-L-His-Gly-L-His-D-Pro-Aib-L-Ser-Gly-L-Ser-NH₂ 
• 1196043-42-1 CbzNH-L-Asp-Gly-L-His-D-Pro-Aib-L-His-Gly-L-His-NH₂ 
• 1196043-46-5 CbzNH-L-Ser-Gly-L-His-D-Pro-Aib-L-Ser-Gly-L-His-NH₂ 
• 1196043-44-3 CbzNH-L-Ser-Gly-L-Ser-D-Pro-Aib-L-His-Gly-L-His-NH₂ 

Relevant articles and documents

Radical-Mediated Activation of Esters with a Copper/Selectfluor System: Synthesis of Bulky Amides and Peptides

Herein, we describe a new approach for the activation of esters via a radical-mediated process enabled by a copper/Selectfluor system. A variety of para-methoxybenzyl esters derived from bulky carboxylic acids and amino acids can be easily converted into the corresponding acyl fluorides, directly used in the one-pot synthesis of amides and peptides. As a proof of concept, this method was applied to the iterative formation of sterically hindered amide bonds.

GLP-1 PRODRUGS

The invention relates to a GLP-1 prodrug of the general formula I: R1-(NHXaa1)-Xaa2-(OHis)-(GLP-1 peptide) (Formula I), wherein GLP-1 peptide is GLP-1(8-37) (SEQ ID NO: 1) or an analogue thereof having a maximum of nine amino acid changes as compared to GLP-1(8-37), R1 is lower alkyl, (NHXaa1) is an amino acid, Xaa2 is an amino acid, and (OHis) is a radical of imidazole-lactic acid; or a pharmaceutically acceptable salt, amide, or ester of the prodrug. The invention also relates to specific GLP-1 parent drugs of the general formula II: (HOHis)-(GLP-1 peptide) (Formula II), as well as specific intermediate products. The invention furthermore relates to a method of achieving release in vivo of an active and stabilised GLP-1 parent drug of the general formula II: (HOHis)-(GLP-1 peptide), by administering a GLP-1 prodrug; as well as to such GLP-1 prodrug, and such GLP-1 parent drug, respectively, for use as a medicament, in particular for use in the treatment and/or prevention of all forms of diabetes and related diseases. The prodrug may be used to alter the PK and/or absorption profile of the drug, for example to a desirable bell-shaped curve. The parent drug has a good biological activity, and is stabilised against degradation by DPP-IV.

A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids

The study describes a new "one-pot" route to the synthesis of N-9-fluorenylmethyloxycarbonyl (Fmoc) α-amino diazoketones. The procedure was tested on a series of commercially available free or side-chain protected α-amino acids employed as precursors. The conversion into the title compounds was achieved by masking and activating the α-amino acids with a single reagent, namely, 9-fluorenylmethyl chloroformate (Fmoc-Cl). The resulting N-protected mixed anhydrides were reacted with diazomethane to lead to the α-amino diazoketones, which were isolated by flash column chromatography in very good to excellent overall yields. The versatility of the procedure was verified on lipophilic α-amino acids and further demonstrated by the preparation of N-Fmoc-α-amino diazoketones also from α-amino acids containing side-chain masking groups, which are orthogonal to the Fmoc one. The results confirmed that tert-butyloxycarbonyl (Boc), tert-butyl (tBu), and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf), three acid-labile protecting groups mostly adopted in the solution and solid-phase peptide synthesis, are compatible to the adopted reaction conditions. In all cases, the formation of the corresponding C-methyl ester of the starting amino acid was not observed. Moreover, the proposed method respects the chirality of the starting α-amino acids. No racemization occurred when the procedure was applied to the synthesis of the respective N-Fmoc-protected α-amino diazoketones from l-isoleucine and l-threonine and to the preparation of a diastereomeric pair of N-Fmoc-protected dipeptidyl diazoketones.

Exploiting an inherent neighboring group effect of α-amino acids to synthesize extremely hindered dipeptides

The creation of highly hindered peptides that contain combinations of non-natural N-alkyl amino acids and N-alkyl-α,α-disubstituted amino acids presents a formidable challenge. Hindered, non-natural amino acids are of interest because they import resistance to proteolysis and unusual conformational properties to peptides that contain them. Toward a solution to this problem, we describe a new approach to creating extremely hindered dipeptides that is operationally simple and uses mild conditions and commercially available amino acids. The approach reduces the need for protecting groups and yields urethane-protected dipeptide acids that can be used as building blocks in the synthesis of larger peptides. We propose that the reaction proceeds through a previously unexploited intramolecular O,N-acyl transfer pathway. Copyright

Highly selective deprotection of tert-butyl esters using ytterbium triflate as a catalyst under mild conditions

Ytterbium triflate catalyses the deprotection of tert-butyl esters selectively in the presence of other esters under mild conditions in almost quantitative yields. The reactions are carried out in nitromethane (45°-50°C) using 5 mole percent of the catalyst.

Zinc promoted rapid and efficient synthesis of Fmoc- and Z-α,α-dialkylamino acids under neutral conditions

The introduction of Nα-9-fluorenylmethyloxycarbonyl (Fmoc) and benzyloxycarbonyl (Z) groups into α,α-dialkylamino acids is described at neutral pH using Fmoc-Cl or Z-Cl as an acylating agent respectively in the presence of activated zing powder. The reaction is simple, fast and clean. It also permits the scale up with high yields. It is completely free from protected oligomer formation, which is a known side-reaction when Schotten-Baumann procedure is followed. All the Fmoc- and Z-amino acids prepared have been fully characterized.

DNA-binding ligands from peptide libraries containing unnatural amino acids

An unnatural peptide-based library, bound on a solid support, was screened for double-stranded-DNA (dsDNA)-binding ligands. For this purpose, fluorescein and rhodamine were used to label the single-stranded oigodeoxynucleotides. Beads containing products with affinity to dsDNA turned red in visible light and fluoresced yellow in UV light. A similar technique can be used for the selection of ligands which bind to a hairpin RNA, using a monolabelled oligoribonucleotide. The screening process revealed a high structure-affinity relationship in the successful products. Only six out of the twelve unnatural amino acids were selected, with the repeated appearance of AlaU, Sar and the secondary amino acids (Hyp, Inp). The affinity and selectivity for the target was determined using a DNase I protection assay.