Analogues of both Leu- and Met-enkephalin containing a constrained dipeptide isostere prepared from a Baylis-Hillman adduct

Roberta Galeazzi; Gianluca Martelli; Eleonora Marcucci; Mario Orena; Samuele Rinaldi; Roberta Lattanzi; Lucia Negri

doi:10.1007/s00726-009-0314-z

Analogues of both Leu- and Met-enkephalin containing a constrained dipeptide isostere prepared from a Baylis-Hillman adduct

Roberta Galeazzi, Gianluca Martelli, Eleonora Marcucci, Mario Orena, Samuele Rinaldi, Roberta Lattanzi, Lucia Negri

Istituto Nazionale di Riposo e Cura per Anziani V.E. II

Research output: Contribution to journal › Article › peer-review

Abstract

An efficient route was developed for the synthesis of the Fmoc-protected dipeptide 4, isostere of Gly-Gly containing an α-methylene β-amino acid; the conformationally restricted analogues of Leu-enkephalin, 3a, and Met-enkephalin, 3b, respectively, were prepared by changing 4 for Gly ²-Gly³ in the native compounds 3a and 3b whose biological activities were significantly lower than the parent compounds.

Original language	English
Pages (from-to)	1057-1065
Number of pages	9
Journal	Amino Acids
Volume	38
Issue number	4
DOIs	https://doi.org/10.1007/s00726-009-0314-z
Publication status	Published - Apr 2010

Keywords

Activity
Baylis-Hillman
Conformational restriction
Dipeptide
Isostere

ASJC Scopus subject areas

Biochemistry
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1007/s00726-009-0314-z

Cite this

@article{843326c8f46143fab38acf338098189a,

title = "Analogues of both Leu- and Met-enkephalin containing a constrained dipeptide isostere prepared from a Baylis-Hillman adduct",

abstract = "An efficient route was developed for the synthesis of the Fmoc-protected dipeptide 4, isostere of Gly-Gly containing an α-methylene β-amino acid; the conformationally restricted analogues of Leu-enkephalin, 3a, and Met-enkephalin, 3b, respectively, were prepared by changing 4 for Gly 2-Gly3 in the native compounds 3a and 3b whose biological activities were significantly lower than the parent compounds.",

keywords = "Activity, Baylis-Hillman, Conformational restriction, Dipeptide, Isostere",

author = "Roberta Galeazzi and Gianluca Martelli and Eleonora Marcucci and Mario Orena and Samuele Rinaldi and Roberta Lattanzi and Lucia Negri",

year = "2010",

month = apr,

doi = "10.1007/s00726-009-0314-z",

language = "English",

volume = "38",

pages = "1057--1065",

journal = "Amino Acids",

issn = "0939-4451",

publisher = "Springer Wien",

number = "4",

}

TY - JOUR

T1 - Analogues of both Leu- and Met-enkephalin containing a constrained dipeptide isostere prepared from a Baylis-Hillman adduct

AU - Galeazzi, Roberta

AU - Martelli, Gianluca

AU - Marcucci, Eleonora

AU - Orena, Mario

AU - Rinaldi, Samuele

AU - Lattanzi, Roberta

AU - Negri, Lucia

PY - 2010/4

Y1 - 2010/4

N2 - An efficient route was developed for the synthesis of the Fmoc-protected dipeptide 4, isostere of Gly-Gly containing an α-methylene β-amino acid; the conformationally restricted analogues of Leu-enkephalin, 3a, and Met-enkephalin, 3b, respectively, were prepared by changing 4 for Gly 2-Gly3 in the native compounds 3a and 3b whose biological activities were significantly lower than the parent compounds.

AB - An efficient route was developed for the synthesis of the Fmoc-protected dipeptide 4, isostere of Gly-Gly containing an α-methylene β-amino acid; the conformationally restricted analogues of Leu-enkephalin, 3a, and Met-enkephalin, 3b, respectively, were prepared by changing 4 for Gly 2-Gly3 in the native compounds 3a and 3b whose biological activities were significantly lower than the parent compounds.

KW - Activity

KW - Baylis-Hillman

KW - Conformational restriction

KW - Dipeptide

KW - Isostere

UR - http://www.scopus.com/inward/record.url?scp=77951665241&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77951665241&partnerID=8YFLogxK

U2 - 10.1007/s00726-009-0314-z

DO - 10.1007/s00726-009-0314-z

M3 - Article

C2 - 19585218

AN - SCOPUS:77951665241

SN - 0939-4451

VL - 38

SP - 1057

EP - 1065

JO - Amino Acids

JF - Amino Acids

IS - 4

ER -

Analogues of both Leu- and Met-enkephalin containing a constrained dipeptide isostere prepared from a Baylis-Hillman adduct

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this