123884-01-5

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 73818-55-0 Bestmann ylide 
• 63-91-2 L-phenylalanine 
• 112700-41-1 (5S)-5-benzyl-1-(tert-butyloxycarbonyl)-4-hydroxy-1,5-dihydro-pyrrol-2-one 
• 109579-08-0 (S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 110104-60-4 (E)-4-chloro-3-methoxy-but-2-enoic acid methyl ester 
• 1268345-08-9 (S)-5-benzyl-1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268345-03-4 (S)-5-benzyl-1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-85-9 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268344-84-8 1-[(R)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 

Downstream Products

• 1268345-11-4 C₂₂H₂₄N₂O₃ 
• 1268345-12-5 N-Boc-L-Val-N-Me-L-Val-N-Me-L-Phe-Dpy 
• 1268345-13-6 L-Val-N-Me-L-Val-N-Me-L-Phe-Dpy 
• 1268345-10-3 C₂₇H₃₂N₂O₅ 

Relevant academic research and scientific papers

Synthesis and anticancer activity of the proposed structure of caldoramide, an N-peptidyltetramate from the cyanobacterium Caldora penicillata

The structure proposed in the literature for caldoramide, a formal pentapeptide metabolite of the marine cyanobacterium Caldora penicillata, was synthesised in 12 steps and 16% yield (longest linear sequence from isoleucine) following the strategy of a stepwise consecutive extension of an N-oligopeptidyl chain on a tetramate anchor. The synthetic product differed from the natural isolate in optical rotation, some NMR data, and cytotoxicities. Its antiproliferative effect on three human cancer cell lines was distinctly lower than that of related dolastatin 10 and belamide A.

Natural dolapyrrolidone: Isolation and absolute stereochemistry of a substructure of bioactive peptides

During the course of our chemical analysis of the hydrophilic fractions from marine cyanobacterium Moorena producens, we have isolated natural dolapyrrolidone (Dpy, 1), a natural pyrrolidone derived from phenylalanine, for the first time as a single compound. Compound 1, with an (S)-l absolute stereochemistry, was previously identified as a substructure that is common among several bioactive natural peptides. Surprisingly, the absolute stereochemistry of the isolated natural 1, determined through total synthesis, was (R)-d. This result was unambiguously determined by HPLC analysis using a chiral stationary column by comparing the retention times of the natural 1 and authentic samples of synthetic enantiomers. To verify the unexpected result, the absolute stereochemistry of the natural 1 was confirmed by X-ray crystallographic analysis of Pt-complex derivative using the synthetic enantiomer.

Total synthesis of modified pentapeptide, caldoramide

Total synthesis of modified pentapeptide, caldoramide, a cytotoxic linear pentapeptide from the marine cyanobacterium Caldora penicillate is described. Notable features of the route include the efficient preparation of three key fragments and final assemb

A flexible asymmetric approach to methyl 5-alkyltetramates and its application in the synthesis of cytotoxic marine natural product belamide A

By using a methyl tetramate derivative (R)- or (S)-9 as a novel chiral building block, a direct, flexible, and highly enantioselective approach to methyl (R)- or (S)-5-alkyltetramates (2) is disclosed. Among the synthesized methyl 5-alkyltetramates 2, met