135226-83-4

Upstream product

• 135226-82-3 3-acetyl-N,O-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine methyl ester 
• 110774-03-3 L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester 

Downstream Products

• 135226-84-5 3-hydroxy-N,O-dimethyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine methyl ester 
• 135226-85-6 N,O⁴-dimethyl-L-DOPA methyl ester 
• 135226-89-0 methyl 4-methoxy-12-amino>-N¹⁰-methyl-11-oxo-2-azatricyclo<12.2.2.1^3,7>nonadeca-3,5,7(19),14,16,17-hexaene-9-carboxylate 
• 64725-24-2 deoxybouvadin 
• 122621-60-7 RA-VII 
• 135226-91-4 C₄₆H₆₀N₆O₁₂ 
• 135226-90-3 BOC-D-alanyl-L-alanyl-N,O-dimethyl-L-tyrosyl-L-alanyl-N-methyl-L-tyrosyl-N,O-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester 
• 135226-88-9 (S)-2-{[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-(4-iodo-phenyl)-propionyl]-methyl-amino}-3-(3-hydroxy-4-methoxy-phenyl)-propionic acid methyl ester 
• 109011-07-6 C₄₁H₅₂N₆O₁₀ 
• 167316-09-8 BOC-D-alanyl-L-alanyl-N,O⁴-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester 
• 167316-10-1 BOC-D-alanyl-L-alanyl-O⁴-methyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester 
• 167316-15-6 C₄₅H₅₈N₆O₁₂ 
• 167316-16-7 C₄₄H₅₆N₆O₁₂ 
• 167316-03-2 3-acetoxy-N,O-dimethyl-N-<<(tert-butyloxy)carbonyl>-L-4'-iodophenylalanyl>-L-tyrosine methyl ester 

Relevant academic research and scientific papers

Synthesis of new DOPA derivative from l-tyrosine for construction of bioactive compound

A practical synthetic method of new DOPA derivative was developed with L-tyrosine as starting material. The new DOPA analogue could be used in building bioactive compounds.

Total synthesis of cycloisodityrosine, RA-VII, deoxybouvardin, and N29-desmethyl-RA-VII: Identification of the pharmacophore and reversal of the subunit functional roles

Full details of a concise total synthesis of RA-VII (1) and deoxybouvardin (2) are described based on the implementation of an effective intramolecular Ullmann reaction as the key macrocyclization reaction in the preparation of the elusive 14-membered cycloisodityrosine subunit (33) of the bicyclic hexapeptides. Subsequent coupling of 34 to tetrapeptide 17 and macrocyclization with C2-N3 amide bond formation provided 1 and 2. In efforts that address the key structural and conformational features of the agents that contribute to their antitumor activity, N29-desmethyl-RA-VII was prepared and its chemical, conformational, and preliminary biological properties are detailed. The comparable conformational features of N29-desmethyl-RA-VII and RA-VII including a characteristic cis C30-N29 amide bond suggest that the tetrapeptide housed within the 18-membered ring induces the 14-membered cycloisodityrosine to adopt a conformation possessing an inherently disfavored cis secondary or tertiary amide. Moreover, in contrast to prior suppositions in which the rigid 14-membered ring of N-methylcycloisodityrosine has been suggested to serve the functional role of inducing a rigid, normally inaccessible conformation within the biologically relevant D-Ala-Ala-N-Me-Tyr-(OMe)-Ala tetrapeptide, experimental studies demonstrating that the intrinsic activity of the agents resides within the cycloisodityrosine subunit are presented. Thus, the results of the experimental studies require a reversal of the functional roles of the subunits of the agents in which it is the tetrapeptide housed within the 18-membered ring that potentiates the inherent biological properties and alters the conformation of cycloisodityrosine.