- The synthesis of Nα-protected amino hydroxamic acids from Nα-protected amino acids employing versatile chlorinating agent CPI-Cl
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Racemization free synthesis of Nα-protected amino hydroxamic acids from Nα-protected amino acids employing the versatile chlorinating reagent CPI-Cl has been described in one-pot. The present protocol has shown compability towards urethane protecting groups like Boc, Cbz and Fmoc, and side chain protections of amino acids showed complete tolerance.
- Vathsala,Srinivasulu,Santhosh,Sureshbabu, Vommina V.
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- Eco-friendly synthesis of peptides using fmoc-amino acid chlorides as coupling agent under biphasic condition
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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.
- Kantharaju, Kamanna,Khatavi, Santosh Y.
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p. 699 - 707
(2021/08/23)
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- HOAt.DCHA as co-coupling agent in the synthesis of peptides employing Fmoc-amino acid chlorides as coupling agents: Application to the synthesis of ss-casomorphin
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A simple, efficient and racemization free method for the synthesis of peptides employing Fmoc-amino acid chlorides mediated by HOAtDCHA as a co-coupling agent has been described. This protocol is successfully employed in the synthesis of the pentapeptide H-Pro-Gly-VaI-GIy-VaI-OH (PGVGV), and ss-casomorphin (H-Tyr-Pro-Phe-Pro-Gly-OH) in 85 and 80% yields, respectively.
- Sureshbabu, Vommina V.,Chennakrishnareddy, Gundala
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experimental part
p. 981 - 988
(2009/12/28)
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- (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid azides: Synthesis, isolation, characterisation, stability and application to synthesis of peptides
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The synthesis of Fmoc amino acid azides starting from the corresponding protected amino acid and sodium azide (NaN3) by the mixed anhydride method using isobutoxycarbonyl chloride (IBC-Cl) or by the acid chloride method is described. Isolated as crystalli
- Babu, Vommina V. Suresh,Ananda, Kuppanna,Vasanthakumar, Ganga-Ramu
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p. 4328 - 4331
(2007/10/03)
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- Synthesis of peptides mediated by potassium salt of 1-hydroxy-7-azabenzotriazole
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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.
- Gopi, H. N.,Babu, V. V. Suresh
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p. 394 - 396
(2007/10/03)
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