Fmoc-GABA-OH

Base Information

• Chemical Name: Fmoc-GABA-OH
• CAS No.: 116821-47-7
• Molecular Formula: C19H19NO4
• Molecular Weight: 325.364
• Hs Code.: 2924 29 70
• European Community (EC) Number: 832-968-2
• DSSTox Substance ID: DTXSID80373229
• Nikkaji Number: J1.190.307J
• Wikidata: Q72478437
• Mol file: 116821-47-7.mol

Synonyms:116821-47-7;Fmoc-GABA-OH;Fmoc-gamma-Abu-OH;Fmoc-GABA;4-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic Acid;n-fmoc-4-aminobutyric acid;4-(Fmoc-amino)butyric acid;4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid;4-(((9H-Fluoren-9-yl)methoxy)carbonylamino)butanoic acid;Fmoc-4-aminobutanoic acid;Butanoic acid, 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-;MFCD00144889;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-4-aminobutyric Acid;Fmoc-?-Abu-OH;N-Fmoc-DL-4-amino-butyric acid;n-(9-fluorenylmethoxycarbonyl)-4-aminobutyric acid;4-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)BUTANOIC ACID;Fmoc--Abu-OH;Fmoc-Abu(4)-OH;N-Fmoc-g-aminobutyric Acid;4-(Fmoc-amino)butyric acid,;SCHEMBL178801;4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoic acid;DTXSID80373229;ACUIFAAXWDLLTR-UHFFFAOYSA-N;AKOS012614849;AC-12820;BP-28256;DS-13643;Fmoc-GABA-OH, >=97.0% (HPLC);SY051395;CS-0040461;F0911;FT-0654119;EN300-650948;A803679;J-300322;4-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid;4-(9H-Fluorene-9-ylmethoxycarbonylamino)butyric acid;Z1123719993;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-gamma-aminobutyric acid;4-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid;N-Fmoc-4-aminobutyric Acid

Chemical Property of Fmoc-GABA-OH

Chemical Property:

• Appearance/Colour: Colorless and transparent liquid
• Vapor Pressure: 6.43E-14mmHg at 25°C
• Melting Point: 172.0 to 176.0 °C
• Refractive Index: 1.6
• Boiling Point: 571.9 °C at 760 mmHg
• PKA: 4.68±0.10(Predicted)
• Flash Point: 299.7 °C
• PSA: 75.63000
• Density: 1.256 g/cm³
• LogP: 3.78080
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 325.13140809
• Heavy Atom Count: 24
• Complexity: 431

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-γ-aminobutyric acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NCCCC(=O)O
• Description: Fmoc-4-aminobutanoic acid can be used as a PROTAC linker in the synthesis of PROTACs and other conjugation applications. Fmoc-4-aminobutanoic acid is an alkane chian with terminal Fmoc-protected amine and carboxylic acid groups. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.
• Uses: 4-(Fmoc-amino)butyric acid is used in agrochemical, pharmaceutical and dyestuff field.

Technology Process of Fmoc-GABA-OH

There total 7 articles about Fmoc-GABA-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4-amino-n-butyric acid (56-12-2) → N-(9-fluorenylmethyloxycarbonyl)-4-aminobutyric acid (116821-47-7)

Guidance literature:

With water; sodium carbonate; In 1,4-dioxane; for 2.5h;

DOI:10.1002/(SICI)1521-3765(19980310)4:3<425::AID-CHEM425>3.0.CO;2-W

Reference yield: 90.0%

N-(9-fluorenylmethoxycarbonyl)-4-aminobutyric acid 1,1-dimethylallyl ester (851713-93-4) → N-(9-fluorenylmethyloxycarbonyl)-4-aminobutyric acid (116821-47-7)

Guidance literature:

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/ol0476117

Reference yield: 86.4%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + 4-amino-n-butyric acid (56-12-2) → N-(9-fluorenylmethyloxycarbonyl)-4-aminobutyric acid (116821-47-7)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 5 - 20 ℃;

DOI:10.1039/c9ob00014c

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

4-amino-n-butyric acid

methyl 4-(9-fluorenylmethylcarbonyl)amino-butanoate

N-(9-fluorenylmethoxycarbonyl)-4-aminobutyric acid 1,1-dimethylallyl ester

Refernces

• 1、 Aloysius, Herve,Hu, Longqin. "Improving the Specificity of the Prostate-Specific Antigen Substrate Glutaryl-Hyp-Ala-Ser-Chg-Gln as a Promoiety". . p. 837 - 848. Retrieved 2015.
• 2、 Lescrinier, Theo,Hendrix, Chris,Kerremans, Luc,Rozenski, Jef,Link, Andreas,Samyn, Bart,Van Aerschot, Arthur,Lescrinier, Eveline,Eritja, Ramon,Van Beeumen, Jozef,Herdewijn, Piet. "DNA-binding ligands from peptide libraries containing unnatural amino acids". . p. 425 - 433. Retrieved 1998.
• 3、 Bandolik, Jan J.,Bhatia, Sanil,Borkhardt, Arndt,Hamacher, Alexandra,Hansen, Finn K.,Kassack, Matthias U.,Meiler, Jens,Roatsch, Martin,S?nnichsen, Melf,Sch?ler, Andrea,Schoeder, Clara T.,Sinatra, Laura. "Hydroxamic Acids Immobilized on Resins (HAIRs): Synthesis of Dual-Targeting HDAC Inhibitors and HDAC Degraders (PROTACs)". supporting information. p. 22494 - 22499. Retrieved 2020/10/12.
• 4、 -. "NEW PEPTIDE-LINKED ESTER PRODRUGS ACTIVATED BY PROSTATE-SPECIFIC ANTIGEN". Paragraph 64-65. . Retrieved 2018/08/26.