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

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

48 Citations (Scopus)

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.

Original language	English
Pages (from-to)	13319-13322
Number of pages	4
Journal	Chemistry - A European Journal
Volume	23
Issue number	54
DOIs	https://doi.org/10.1002/chem.201703616
Publication status	Published - 27 Sept 2017
Externally published	Yes

!!!Keywords

beta-amino imide
cyclic peptides
cyclol
medium-sized ring
ring expansion

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10.1002/chem.201703616

Cite this

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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",

volume = "23",

pages = "13319--13322",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc",

number = "54",

}

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

Abstract

!!!Keywords

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CCDC 1557947: Experimental Crystal Structure Determination

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Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides

Abstract

!!!Keywords

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Datasets

CCDC 1557947: Experimental Crystal Structure Determination

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