Hybrid alpha/beta-peptides: for-Met-Leu-Phe-OMe analogues containing geminally disubstituted beta2,2- and beta 3,3-amino acids at the central position

A Mollica; M Paglialunga Paradisi; D Torino; S Spisani; G Lucente

doi:10.1007/s00726-006-0260-y

Hybrid alpha/beta-peptides: for-Met-Leu-Phe-OMe analogues containing geminally disubstituted beta2,2- and beta 3,3-amino acids at the central position

Amino Acids. 2006 Jun;30(4):453-9. doi: 10.1007/s00726-006-0260-y. Epub 2006 Mar 20.

Authors

A Mollica¹, M Paglialunga Paradisi, D Torino, S Spisani, G Lucente

Affiliation

¹ Dipartimento di Studi Farmaceutici, Università degli Studi di Roma, La Sapienza, Rome, Italy.

PMID: 16547648
DOI: 10.1007/s00726-006-0260-y

Abstract

The two fMLF-OMe analogues For-Met-beta(3)hAc(6)c-Phe-OMe (6) and For-Met-beta(2)hAc(6)c-Phe-OMe (12) and their corresponding N-Boc derivatives 5 and 11 have been synthesized and their biological activity towards human neutrophils evaluated. The N-formyl peptides 6 and 12 exhibit good activity as chemoattractans and 12 is highly active in superoxide anion production. The preferred solution conformation of the two N-formyl derivatives has been discussed.

Publication types

Comparative Study

MeSH terms

Amino Acids / chemistry*
Humans
Ligands
Molecular Structure
N-Formylmethionine Leucyl-Phenylalanine / analogs & derivatives
N-Formylmethionine Leucyl-Phenylalanine / chemistry*
N-Formylmethionine Leucyl-Phenylalanine / pharmacology
Neutrophils / drug effects*
Peptides / chemical synthesis*
Peptides / chemistry
Peptides / pharmacology*
Protein Structure, Secondary
Structure-Activity Relationship

Substances

Amino Acids
Ligands
Peptides
N-Formylmethionine Leucyl-Phenylalanine