753487-55-7

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 874894-76-5 (2S,3R)-2-amino-3-methoxy-3-phenylpropanoic acid 
• 63-91-2 L-phenylalanine 
• 135395-13-0 (S)-N-(tert-Butyl)-N^α-phthaloylphenylalaninamide 
• 112418-19-6 (R)-2-N-tert-butoxycarbonylamino-3-(tert-butyldimethylsilyloxy)propionic acid methyl ester 
• 124085-68-3 tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate 
• 217661-62-6 [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 1009093-09-7 (2R,3R)-N-Boc-3-methoxy-1-O-(tert-butyldimethylsilyl)-phenylalaninol 
• 1009093-06-4 (2R,3R)-N-Boc-3-methoxy-phenylalaninol 
• 1335232-84-2 (2R,3R)-3-hydroxy-para-nitrophenylalaninol 
• 753487-59-1 (2S,3R)-3-methoxy-N-tert-butyl-N²-phthaloylphenylalanylamide 
• 753488-03-8 2-amino-N-tert-butyl-3-methoxy-3-phenyl-propionamide 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 

Downstream Products

• 1019858-67-3 cyclomarin D 

Relevant academic research and scientific papers

Synthesis of modified β-methoxyphenylalanines via diazonium chemistry and their incorporation in desoxycyclomarin analogues

The marine natural products cyclomarins have remarkable anti-mycobacterial and antiplasmodial activities. The heptapeptic structure of this compound class comprisis four highly interesting non-canonical amino acids, including a rather unusual syn β-methoxyphenylalanine. To get a deeper insight into the structure-activity realtionship of cyclomarines, a straightforward protocol for the stereoselective synthesis of this building block was developed, based on diazonium chemistry.

Total Synthesis of Cyclomarin A, a Marine Cycloheptapeptide with Anti-Tuberculosis and Anti-Malaria Activity

An efficient synthetic protocol for the stereoselective synthesis of cyclomarin A is reported. Key steps in the syntheses of the building blocks are an asymmetric chelate-enolate Claisen rearrangement, an asymmetric hydrogenation, and highly diastereosele

Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities

Cyclomarins are cyclic heptapeptides containing four unusual amino acids. New synthetic protocols toward their synthesis have been developed, leading to the synthesis and biological evaluation of three natural occurring cyclomarins. Interestingly, cyclomarins address two completely different targets: Clp C1, a subunit of the caseinolytic protease of Mycobacterium tuberculosis (MTB), as well as PfAp3Ase of Plasmodium falciparum. Therefore, cyclomarins are interesting lead structures for the development of drugs against tuberculosis and malaria.

Total synthesis of cyclomarin C

The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.