Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/32499
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dc.titleStereochemical Assignment and Total Synthesis of An Antimalarial Lipopeptide
dc.contributor.authorSHIBAJI KUMAR GHOSH
dc.date.accessioned2012-04-30T18:01:45Z
dc.date.available2012-04-30T18:01:45Z
dc.date.issued2011-05-10
dc.identifier.citationSHIBAJI KUMAR GHOSH (2011-05-10). Stereochemical Assignment and Total Synthesis of An Antimalarial Lipopeptide. ScholarBank@NUS Repository.
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/32499
dc.description.abstractMalaria is one of the prime causes that are responsible for the high mortality in this world. As more than 40% of the world?s population lives in malaria endemic areas, it is immediate need to discover cost effective drugs or vaccines for fighting against Plasmodium. falciparum. The lipopeptide (N1708) isolated from Streptomyces sp. exhibits promising activity against P. falciparum (IC50= 0.8 ?M against 3D7 strain). The natural product contains two non-proteinogenic amino acids (each having two stereogenic centers), aspartic acid and a long chain fatty acid (with one chiral centre and one double bond). In this work, we have hydrolysed the natural peptide and compared the natural fragments with that of synthetic amino acid steroisomers (prepared by asymmetric synthesis) using Marfey?s reagent derivatisation technique. This has allowed the configurational assignment of six unknown stereogenic centers. The full structure of N1708 has been confirmed by the total synthesis of the target lipopeptide.
dc.language.isoen
dc.subjectLipopeptide, Asymmetric synthesis, Non-proteinogenic amino acids, Marfey’s reagent, Stereochemical assignment, Total synthesis
dc.typeThesis
dc.contributor.departmentCHEMISTRY
dc.contributor.supervisorLEAR, MARTIN JAMES
dc.description.degreePh.D
dc.description.degreeconferredDOCTOR OF PHILOSOPHY
dc.identifier.isiutNOT_IN_WOS
Appears in Collections:Ph.D Theses (Open)

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