Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides

Rodrigo Mendoza-Sanchez; Victoria B. Corless; Q. Nhu N. Nguyen; Milan Bergeron-Brlek; John Frost; Shinya Adachi; Dean J. Tantillo; Andrei K. Yudin

doi:10.1002/chem.201703616

Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides

Rodrigo Mendoza-Sanchez
, Victoria B. Corless
, Q. Nhu N. Nguyen
, Milan Bergeron-Brlek
, John Frost
, Shinya Adachi
, Dean J. Tantillo
, Andrei K. Yudin

Résultats de recherche: Contribution à un journal › Article publié dans une revue, révisé par les pairs › Revue par des pairs

48 Citations (Scopus)

Résumé

Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In the present study, we report an approach to medium-sized cyclic peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines and offers a straightforward transition from frequently examined scaffolds in drug discovery to a rarely visited class of medium-sized rings.

langue originale	Anglais
Pages (de - à)	13319-13322
Nombre de pages	4
journal	Chemistry - A European Journal
Volume	23
Numéro de publication	54
Les DOIs	https://doi.org/10.1002/chem.201703616
état	Publié - 27 sept. 2017
Modification externe	Oui

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10.1002/chem.201703616

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CCDC 1557947: Experimental Crystal Structure Determination
Mendoza-Sanchez, R. (Créateur), Corless, V. B. (Créateur), Nguyen, Q. N. N. (Créateur), Bergeron-Brlek, M. (Créateur), Frost, J. (Créateur), Adachi, S. (Créateur), Tantillo, D. J. (Créateur) & Yudin, A. K. (Créateur), Cambridge Crystallographic Data Centre, 2017
DOI: 10.5517/ccdc.csd.cc1p95cj
Ensemble de données

Contient cette citation

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title = "Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides",

abstract = "Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In the present study, we report an approach to medium-sized cyclic peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines and offers a straightforward transition from frequently examined scaffolds in drug discovery to a rarely visited class of medium-sized rings.",

keywords = "beta-amino imide, cyclic peptides, cyclol, medium-sized ring, ring expansion",

author = "Rodrigo Mendoza-Sanchez and Corless, \{Victoria B.\} and Nguyen, \{Q. Nhu N.\} and Milan Bergeron-Brlek and John Frost and Shinya Adachi and Tantillo, \{Dean J.\} and Yudin, \{Andrei K.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

month = sep,

day = "27",

doi = "10.1002/chem.201703616",

language = "English",

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journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - Cyclols Revisited

T2 - Facile Synthesis of Medium-Sized Cyclic Peptides

AU - Mendoza-Sanchez, Rodrigo

AU - Corless, Victoria B.

AU - Nguyen, Q. Nhu N.

AU - Bergeron-Brlek, Milan

AU - Frost, John

AU - Adachi, Shinya

AU - Tantillo, Dean J.

AU - Yudin, Andrei K.

PY - 2017/9/27

Y1 - 2017/9/27

N2 - Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In the present study, we report an approach to medium-sized cyclic peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines and offers a straightforward transition from frequently examined scaffolds in drug discovery to a rarely visited class of medium-sized rings.

AB - Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In the present study, we report an approach to medium-sized cyclic peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines and offers a straightforward transition from frequently examined scaffolds in drug discovery to a rarely visited class of medium-sized rings.

KW - beta-amino imide

KW - cyclic peptides

KW - cyclol

KW - medium-sized ring

KW - ring expansion

UR - https://www.scopus.com/pages/publications/85030088861

U2 - 10.1002/chem.201703616

DO - 10.1002/chem.201703616

M3 - Journal Article

C2 - 28771904

AN - SCOPUS:85030088861

SN - 0947-6539

VL - 23

SP - 13319

EP - 13322

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 54

ER -

Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides

Résumé

Accès au document

Autres fichiers et liens

Empreinte digitale

Ensembles de données

CCDC 1557947: Experimental Crystal Structure Determination

Contient cette citation