Biomaterial Database

Synthesis of cyclic and acyclic partial retro-inverso modified enkephalins. 1984

J M Berman, and M Goodman

The cyclic partial retro-inverso modified enkephalins, H-Tyr-cyclo[-D-Glu-Gly-gPhe-D-Leu-] (I), H-Tyr-cyclo[-D-A2bu-Gly-gPhe-R&S-mLeu-] (IIf, IIs), and H-Tyr-cyclo[-D-Glu-Gly-Phe-gLeu-] (III), have been synthesized by solution methodology. In a like manner, their corresponding acyclic analogs Ia-IIIa containing D-Ala2 have also been prepared. Gem-diaminoalkyl residues were generated by conversion of Boc-dipeptide carboxamide to the corresponding gem-diaminoalkyl "dipeptide" salt using [bis(trifluoroacetoxy)iodo] benzene. Cyclizations were achieved at high dilution utilizing diphenylphosphoryl azide as the coupling reagent.

UI	MeSH Term	Description	Entries
D010456	Peptides, Cyclic	Peptides whose amino acid residues are linked together forming a circular chain. Some of them are ANTI-INFECTIVE AGENTS; some are biosynthesized non-ribosomally (PEPTIDE BIOSYNTHESIS, NON-RIBOSOMAL).	Circular Peptide,Cyclic Peptide,Cyclic Peptides,Cyclopeptide,Orbitide,Circular Peptides,Cyclopeptides,Orbitides,Peptide, Circular,Peptide, Cyclic,Peptides, Circular
D011487	Protein Conformation	The characteristic 3-dimensional shape of a protein, including the secondary, supersecondary (motifs), tertiary (domains) and quaternary structure of the peptide chain. PROTEIN STRUCTURE, QUATERNARY describes the conformation assumed by multimeric proteins (aggregates of more than one polypeptide chain).	Conformation, Protein,Conformations, Protein,Protein Conformations
D004745	Enkephalins	One of the three major families of endogenous opioid peptides. The enkephalins are pentapeptides that are widespread in the central and peripheral nervous systems and in the adrenal medulla.	Enkephalin
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships