205498-72-2

Upstream product

• 42417-65-2 Z-MeVal-OH 
• 2812-46-6 proline tert-butyl ester 

Downstream Products

• 1443463-07-7 C₂₀H₂₈N₂O₅ 
• 1256379-74-4 C₂₄H₃₆N₂O₅ 
• 1256379-69-7 C₃₇H₅₁N₃O₈ 
• 1256379-94-8 C₂₆H₃₈N₂O₆ 
• 205498-86-8 ((S)-1-{[(S)-1-((S)-2-{(S)-2-[(1R,2R)-1-Methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-methyl-carbamoyl}-2-methyl-propyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 205498-79-9 C₄₉H₆₉N₇O₈S 
• 205498-84-6 [(S)-1-((S)-2-{(S)-2-[(1R,2R)-1-Methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-methyl-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 205498-76-6 (S)-1-((S)-2-{[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 172837-42-2 (S)-1-((S)-2-{[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid 
• 205498-74-4 (S)-1-{(S)-2-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyryl)-methyl-amino]-3-methyl-butyryl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 205498-80-2 (2R,3R)-3-Methoxy-2-methyl-N-((S)-2-phenyl-1-thiazol-2-yl-ethyl)-3-[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidin-2-yl]-propionamide 

Relevant academic research and scientific papers

Total synthesis and biological evaluation of grassypeptolide A

Herein, we describe in full our investigations into the synthesis of grassypeptolide A (1) in 17 linear steps with an overall yield of 11.3 %. In particular, this work features the late-stage introduction of sensitive bis(thiazoline) heterocycles and 31-membered macrocyclization conducted at the sterically congested secondary amide site in superb conversion (72 % yield). Biological evaluation indicated that grassypeptolide A significantly inhibited cancer cell proliferation in a dose-dependent manner. It induced cancer cell apoptosis, which was associated with increased cleavage of poly(ADP-ribose) polymerase (PARP) and decreased expression of bcl-2 and bcl-xL. Furthermore, grassypeptolide A also caused cell cycle redistribution by increasing cells in the G1 phase and decreasing cells in the S and G2 phases. In addition, cell cycle arrest was correlated with downregulation of cyclin D and upregulation of p27 and p21. Cytotoxic activity: Synthesis of grassypeptolide A, an anticancer marine cyclodepsipeptide, in 17 linear steps with an overall yield of 11.3 % is described (see figure). Subsequent biological evaluation indicated that grassypeptolide A significantly inhibited cancer-cell proliferation in a dose-dependent manner. Copyright

Total synthesis of grassypeptolide

The first total synthesis of grassypeptolide, an anticancer cyclodepsipeptide isolated from marine cyanobacteria, has been achieved in 17 steps and an overall 11.3% yield.

Synthesis and biological activity of chimeric structures derived from the cytotoxic natural compounds dolastatin 10 and dolastatin 15

The natural cytotoxic compounds dolastatins 10 and 15 exhibit great similarities in structure and in their biological activity profiles. Two compounds (1 and 2) formed by interchanging the dolaisoleuine residue of dolastatin 10 and the MeVal-Pro dipeptide