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Peptidomimetics II pp 51–80Cite as

Diketopiperazine-Based Peptide Mimic Scaffolds

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Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 49))

Abstract

2,5-Diketopiperazines (2,5-DKPs) are heterocyclic molecules cyclized from two alpha amino acids. Their ease of synthesis, ability to display up to six functional groups, and pre-organization all led 2,5-DKPs to be utilized in drug discovery, catalysis, and material science. This review focuses on recent developments and applications of the diketopiperazine motif as a rigid scaffold in peptide science to mimic protein secondary structures and in crystal engineering to organize functional groups in three-dimensional space, as well as in molecular recognition and catalysis.

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Abbreviations

Boc:

tert-Butoxycarbonyl

Cbz:

Carboxybenzyl

CD Spectroscopy:

Circular dichroism spectroscopy

CD3OH:

Deuterated methanol

CDCl3 :

Deuterated chloroform

CuAAC:

Cu(I)-catalyzed alkyne–azide cycloaddition

d 6-DMSO:

Deuterated dimethyl sulfoxide

DIC:

Diisopropylcarbodiimide

DIPEA:

N,N-Diisopropylethylamine

DKP:

Diketopiperazine

Fmoc:

9-Fluorenylmethoxycarbonyl

HATU:

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

HBr:

Hydrobromic acid

HOAt:

Hydroxyazabenzotriazole

HUVEC:

Human umbilical vein endothelial cells

MARK:

Mitogen-activated protein kinase

MC/SD simulations:

Monte Carlo/stochastic dynamics simulations

MeIm:

Methylimidazole

MMFF:

Merck molecular force field

MSNT:

1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole

NOE:

Nuclear overhauser effect

NOESY:

Nuclear overhauser effect spectroscopy

ROESY:

Rotating frame nuclear overhauser effect spectroscopy

TFA:

Trifluoroacetic acid

THBC:

Tetrahydro-β-carboline

Trk:

Tropomyosin receptor kinase

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  1. Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, PA, 19122, USA

    Qingquan Zhao & Christian E. Schafmeister

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  1. Qingquan Zhao
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Correspondence to Christian E. Schafmeister .

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  1. Départemente de Chimie, Université de Montréal Départemente de Chimie, MONTREAL, Québec, Canada

    William Lubell

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Zhao, Q., Schafmeister, C.E. (2015). Diketopiperazine-Based Peptide Mimic Scaffolds. In: Lubell, W. (eds) Peptidomimetics II. Topics in Heterocyclic Chemistry, vol 49. Springer, Cham. https://doi.org/10.1007/7081_2015_165

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