210818-40-9

Upstream product

• 142955-51-9 N-butoxycarbonyl-L-phenylalanine anhydride 
• 109-81-9 N-methyl-ethane-1,2-diamine 

Downstream Products

• 210818-41-0 ((R)-2-Benzyloxycarbonylamino-3-{[2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-ethyl]-methyl-amino}-propionylamino)-acetic acid tert-butyl ester 
• 210886-12-7 (S)-2-Amino-N-((6S,12R)-6-benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-yl)-3-(4-hydroxy-phenyl)-propionamide 
• 210818-43-2 [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester 
• 210818-42-1 ((R)-2-[(S)-2-Benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-{[2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-ethyl]-methyl-amino}-propionylamino)-acetic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis and biological activity of a novel methylamine-bridged enkephalin analogue (MABE): A new route to cyclic peptides and peptidomimetics

The synthesis and biological activity of a methylamine-bridged enkephalin analogue (MABE) is presented. The key step in the synthesis of the target compound involves the ring opening of Cbz-D-serine β-lactone with Boc-Phe-NHCH2CH2NHCH3. Further synthetic elaboration of the resulting building block yielded compound 1 (MABE, Tyr-c[(N(β)CH3)-D-A2pr-Gly-Phe- NHCH2-CH2-], where A2pr is a 2,3-diaminopropionic acid residue). Utilizing a combination of NMR and molecular modeling, the structure-biological activity relationships for compound 1 were studied. Using an in vitro isolated receptor assay, MABE was found to have affinities for isolated μ, δ, and κ opioid receptors of 1.6, 2.1, and 340 nM, respectively. By an in vivo thermal escape assay, MABE was found to have an ED50 of 0.027 μg in the rat when administered intrathecally. This effect was reversed by naloxone. By comparison, DAMGO, morphine, and DPDPE were found to yield ED50 values of 0.14, 2.4, and 54 μg, respectively, in the same assay.