211372-13-3Relevant academic research and scientific papers
Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow
Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan
supporting information, (2022/01/06)
Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i
Eco-friendly synthesis of peptides using fmoc-amino acid chlorides as coupling agent under biphasic condition
Kantharaju, Kamanna,Khatavi, Santosh Y.
, p. 699 - 707 (2021/08/23)
Background: Agro-waste derived solvent media act as a greener process for the peptide bond formation using Nα-Fmoc-amino acid chloride and amino acid ester salt with in situ neutralization and coupling under biphasic condition. The Fmoc-amino acid chlorides are prepared by the reported procedure of freshly distilled SOCl2 with dry CH2Cl2. The protocol found many added ad-vantages such as neutralization of amino acid ester salt and not required additional base for the neu-tralization, and directly coupling take place with Fmoc-amino acid chloride gave final product dipeptide ester in good to excellent yields. The protocol occurs with complete stereo chemical integrity of the configuration of substrates. Here, we revisited Schotten-Baumann condition, instead of using inorganic base. Objective: To develop green protocol for the synthesis of peptide bond using Fmoc-amino acid chloride with amino acid esters salt. Methods: The final product isolated is analyzed in several spectroscopic and analytical techniques such as FT-IR,1H-,13C-NMR, Mass spectrometry and RP-HPLC to check stereo integrity and puri-ty of the product. Conclusion: The present method developed greener using natural agro-waste (lemon fruit shell ash) derived solvent medium for the reaction and not required chemical entity.
HOBt·DCHA-mediated synthesis of sterically hindered peptides employing Fmoc-amino acid chlorides in both solution-phase and solid phase methods
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Chenna Krishna
, p. 2625 - 2637 (2008/12/22)
The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF-CH2Cl2 has also been outlined. The final peptide was obtained in 80% yield and was fully characterized. Copyright Taylor & Francis Group, LLC.
Rapid and efficient synthesis of peptide fragments containing α- aminoisobutyric acid using Fmoc-amino acid chlorides/potassium salt of 1- hydroxybenzotriazole
Suresh Babu, Vommina V.,Gopi, Hosahudya N.
, p. 1049 - 1050 (2007/10/03)
The synthesis of peptides containing multiple Aib residues was accomplished using Fmoc-Aib-Cl in presence of KOBt. As no additional base was added, the duration of coupling reactions could be extended. Thus, the synthesis of the alamethicin 1-4 fragment, Aib-Pro-Aib-Ala, the emerimicin 2- 6 fragment, Aib-Aib-Aib-Val-Gly and the Aib tetramer, Fmoc-(Aib)4-OBzl were accomplished in good yield and purity.
Synthesis of peptides mediated by potassium salt of 1-hydroxy-7-azabenzotriazole
Gopi, H. N.,Babu, V. V. Suresh
, p. 394 - 396 (2007/10/03)
The potassium salt of 1-hydroxy-7-azabenzotriazole can be used along with acid chlorides of 9-fluorenylmethyloxycarbonylamino acids as coupling agents in peptide bond formation.The acylation reactions are rapid and efficient and can be carried out in an organic medium.The yields as well as purity of the peptides are satisfactory.
