Synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin scaffold

Sebastien G. Gouin; Paul V. Murphy

doi:10.1021/jo051454n

Synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin scaffold

Sebastien G. Gouin
, Paul V. Murphy

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

20 Citations (Scopus)

Abstract

A novel synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin (DMJ) scaffold has been developed. This involved development of a route suitable for the strategic grafting of pharmacophoric tryptophan and lysine side chains to the nitrogen atom of the piperidine ring and to the primary hydroxyl group of DMJ, respectively. The novel peptidomimetics were found to bind with higher affinity to sst4 receptors than to sst5 receptors.

Original language	English
Pages (from-to)	8527-8532
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	70
Issue number	21
DOIs	https://doi.org/10.1021/jo051454n
Publication status	Published - 14 Oct 2005
Externally published	Yes

Access to Document

10.1021/jo051454n

Cite this

@article{c0d8f253bd524effba436ee505d15e0e,

title = "Synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin scaffold",

abstract = "A novel synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin (DMJ) scaffold has been developed. This involved development of a route suitable for the strategic grafting of pharmacophoric tryptophan and lysine side chains to the nitrogen atom of the piperidine ring and to the primary hydroxyl group of DMJ, respectively. The novel peptidomimetics were found to bind with higher affinity to sst4 receptors than to sst5 receptors.",

author = "Gouin, \{Sebastien G.\} and Murphy, \{Paul V.\}",

year = "2005",

month = oct,

day = "14",

doi = "10.1021/jo051454n",

language = "English",

volume = "70",

pages = "8527--8532",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin scaffold

AU - Gouin, Sebastien G.

AU - Murphy, Paul V.

PY - 2005/10/14

Y1 - 2005/10/14

N2 - A novel synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin (DMJ) scaffold has been developed. This involved development of a route suitable for the strategic grafting of pharmacophoric tryptophan and lysine side chains to the nitrogen atom of the piperidine ring and to the primary hydroxyl group of DMJ, respectively. The novel peptidomimetics were found to bind with higher affinity to sst4 receptors than to sst5 receptors.

AB - A novel synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin (DMJ) scaffold has been developed. This involved development of a route suitable for the strategic grafting of pharmacophoric tryptophan and lysine side chains to the nitrogen atom of the piperidine ring and to the primary hydroxyl group of DMJ, respectively. The novel peptidomimetics were found to bind with higher affinity to sst4 receptors than to sst5 receptors.

UR - https://www.scopus.com/pages/publications/26844450128

U2 - 10.1021/jo051454n

DO - 10.1021/jo051454n

M3 - Article

SN - 0022-3263

VL - 70

SP - 8527

EP - 8532

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Synthesis of somatostatin mimetics based on the 1-deoxymannojirimycin scaffold

Abstract

Access to Document

Other files and links

Fingerprint

Cite this