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Eco-Friendly Synthesis of Peptides Using Fmoc-Amino Acid Chlorides as Coupling Agent Under Biphasic Condition

Author(s):

Santosh Y. Khatavi and K. Kantharaju*   Pages 1 - 9 ( 9 )

Abstract:


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 advantages such as neutralization of amino acid ester salt and not required additional base for the neutralization, 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-, 13CNMR, Mass spectrometry and RP-HPLC to check stereo integrity and purity 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.

Keywords:

Agro-waste, peptide, green chemistry, racemization free, Fmoc-amino acid chloride, neutralization.

Affiliation:

Department of Chemistry, Peptide and Medicinal Chemistry Research Laboratory, Rani Channamma University, Belagavi, P-B, NH-4, 591156, Karnataka, Department of Chemistry, Peptide and Medicinal Chemistry Research Laboratory, Rani Channamma University, Belagavi, P-B, NH-4, 591156, Karnataka



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