Biomimetic synthesis of the IDO inhibitors exiguamine A and B

Matthew Volgraf, Jean Philip Lumb, Harry C. Brastianos, Gavin Carr, Marco K.W. Chung, Martin Münzel, A. Grant Mauk, Raymond J. Andersen, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Biomimetic synthesis is an attempt to assemble natural products along biosynthetic lines without recourse to the full enzymatic machinery of nature. We exemplify this with a total synthesis of exiguamine A and the newly isolated natural product exiguamine B. The most noteworthy feature of this work is an oxidative endgame drawing from the complex chemistry of catecholamines, which allows for ready access to a new class of nanomolar indoleamine-2,3-dioxygenase inhibitors.

Original languageEnglish (US)
Pages (from-to)535-537
Number of pages3
JournalNature Chemical Biology
Volume4
Issue number9
DOIs
StatePublished - 2008

Fingerprint

Biomimetics
Biological Products
Indoleamine-Pyrrole 2,3,-Dioxygenase
Catecholamines
exiguamine B
exiguamine A

ASJC Scopus subject areas

  • Molecular Biology
  • Cell Biology

Cite this

Volgraf, M., Lumb, J. P., Brastianos, H. C., Carr, G., Chung, M. K. W., Münzel, M., ... Trauner, D. (2008). Biomimetic synthesis of the IDO inhibitors exiguamine A and B. Nature Chemical Biology, 4(9), 535-537. https://doi.org/10.1038/nchembio.107

Biomimetic synthesis of the IDO inhibitors exiguamine A and B. / Volgraf, Matthew; Lumb, Jean Philip; Brastianos, Harry C.; Carr, Gavin; Chung, Marco K.W.; Münzel, Martin; Mauk, A. Grant; Andersen, Raymond J.; Trauner, Dirk.

In: Nature Chemical Biology, Vol. 4, No. 9, 2008, p. 535-537.

Research output: Contribution to journalArticle

Volgraf, M, Lumb, JP, Brastianos, HC, Carr, G, Chung, MKW, Münzel, M, Mauk, AG, Andersen, RJ & Trauner, D 2008, 'Biomimetic synthesis of the IDO inhibitors exiguamine A and B', Nature Chemical Biology, vol. 4, no. 9, pp. 535-537. https://doi.org/10.1038/nchembio.107
Volgraf M, Lumb JP, Brastianos HC, Carr G, Chung MKW, Münzel M et al. Biomimetic synthesis of the IDO inhibitors exiguamine A and B. Nature Chemical Biology. 2008;4(9):535-537. https://doi.org/10.1038/nchembio.107
Volgraf, Matthew ; Lumb, Jean Philip ; Brastianos, Harry C. ; Carr, Gavin ; Chung, Marco K.W. ; Münzel, Martin ; Mauk, A. Grant ; Andersen, Raymond J. ; Trauner, Dirk. / Biomimetic synthesis of the IDO inhibitors exiguamine A and B. In: Nature Chemical Biology. 2008 ; Vol. 4, No. 9. pp. 535-537.
@article{7230e3d3f941482480eb71a687adcfde,
title = "Biomimetic synthesis of the IDO inhibitors exiguamine A and B",
abstract = "Biomimetic synthesis is an attempt to assemble natural products along biosynthetic lines without recourse to the full enzymatic machinery of nature. We exemplify this with a total synthesis of exiguamine A and the newly isolated natural product exiguamine B. The most noteworthy feature of this work is an oxidative endgame drawing from the complex chemistry of catecholamines, which allows for ready access to a new class of nanomolar indoleamine-2,3-dioxygenase inhibitors.",
author = "Matthew Volgraf and Lumb, {Jean Philip} and Brastianos, {Harry C.} and Gavin Carr and Chung, {Marco K.W.} and Martin M{\"u}nzel and Mauk, {A. Grant} and Andersen, {Raymond J.} and Dirk Trauner",
year = "2008",
doi = "10.1038/nchembio.107",
language = "English (US)",
volume = "4",
pages = "535--537",
journal = "Nature Chemical Biology",
issn = "1552-4450",
publisher = "Nature Publishing Group",
number = "9",

}

TY - JOUR

T1 - Biomimetic synthesis of the IDO inhibitors exiguamine A and B

AU - Volgraf, Matthew

AU - Lumb, Jean Philip

AU - Brastianos, Harry C.

AU - Carr, Gavin

AU - Chung, Marco K.W.

AU - Münzel, Martin

AU - Mauk, A. Grant

AU - Andersen, Raymond J.

AU - Trauner, Dirk

PY - 2008

Y1 - 2008

N2 - Biomimetic synthesis is an attempt to assemble natural products along biosynthetic lines without recourse to the full enzymatic machinery of nature. We exemplify this with a total synthesis of exiguamine A and the newly isolated natural product exiguamine B. The most noteworthy feature of this work is an oxidative endgame drawing from the complex chemistry of catecholamines, which allows for ready access to a new class of nanomolar indoleamine-2,3-dioxygenase inhibitors.

AB - Biomimetic synthesis is an attempt to assemble natural products along biosynthetic lines without recourse to the full enzymatic machinery of nature. We exemplify this with a total synthesis of exiguamine A and the newly isolated natural product exiguamine B. The most noteworthy feature of this work is an oxidative endgame drawing from the complex chemistry of catecholamines, which allows for ready access to a new class of nanomolar indoleamine-2,3-dioxygenase inhibitors.

UR - http://www.scopus.com/inward/record.url?scp=49949089657&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=49949089657&partnerID=8YFLogxK

U2 - 10.1038/nchembio.107

DO - 10.1038/nchembio.107

M3 - Article

C2 - 18677305

AN - SCOPUS:49949089657

VL - 4

SP - 535

EP - 537

JO - Nature Chemical Biology

JF - Nature Chemical Biology

SN - 1552-4450

IS - 9

ER -