β-Substituted phenylalanine derivatives and toward the total synthesis of callipeltin A

Benjamin S Barth, Purdue University

Abstract

Callipeltin A is a novel cyclic despsipeptide possessing a range of biological activities including anti-HIV, antifungal, and cytotoxicity against select human carcinoma cell lines. Callipeltin A contains several structurally interesting non-proteinogenic amino acids including, (2R,3R,4 S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE), (3 S,4R)-3,4-dimethyl-L-glutamine (DiMeGln), and (2 R,3R)-β-methoxytyrosine (β-MeOTyr). For synthetic and conformational studies on callipeltin A, a variety of β-MeOTyr analogs were synthesized. Additionally, intermediates of AGDHE, TMHEA, DiMeGln, and D-allo-Thr were synthesized with required protecting groups and studies toward the total synthesis of callipeltin A were performed.

Degree

Ph.D.

Advisors

Lipton, Purdue University.

Subject Area

Biochemistry|Organic chemistry

COinS