Rhodium-Catalyzed Regioselective C7Ar-Functionalization of Tryptophan with Quinones and its Late Stage Peptide Exemplification

Disha Harsukhbhai Tank; Narendra Dinkar Kharat; Kiran Bajaj; Siva S. Panda; Rajeev Sakhuja

doi:10.1002/ajoc.202300503

Rhodium-Catalyzed Regioselective C7_Ar-Functionalization of Tryptophan with Quinones and its Late Stage Peptide Exemplification

Disha Harsukhbhai Tank, Narendra Dinkar Kharat, Kiran Bajaj, Siva S. Panda, Rajeev Sakhuja

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

1 Scopus citations

Abstract

Pivaloyl-directed Rh(III)-catalyzed regioselective C7_Ar-H functionalization of protected tryptophans were accomplished with 1,4-benzoquinones, furnishing a series of quinone-appended tryptophan-based unnatural amino acids in high yields. Further, the late stage functionalization on tryptophan-containing dipeptides was achieved with 1,4-benzoquinones in moderate reactivity.

Original language	English (US)
Article number	e202300503
Journal	Asian Journal of Organic Chemistry
Volume	12
Issue number	12
DOIs	https://doi.org/10.1002/ajoc.202300503
State	Published - Dec 2023
Externally published	Yes

Keywords

Functionalization
Metal-Catalysis
Peptides
Regioselectivity
Tryptophan

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1002/ajoc.202300503

Cite this

@article{ccb908bfc5a542ce9a30f90d4d397b83,

title = "Rhodium-Catalyzed Regioselective C7Ar-Functionalization of Tryptophan with Quinones and its Late Stage Peptide Exemplification",

abstract = "Pivaloyl-directed Rh(III)-catalyzed regioselective C7Ar-H functionalization of protected tryptophans were accomplished with 1,4-benzoquinones, furnishing a series of quinone-appended tryptophan-based unnatural amino acids in high yields. Further, the late stage functionalization on tryptophan-containing dipeptides was achieved with 1,4-benzoquinones in moderate reactivity.",

keywords = "Functionalization, Metal-Catalysis, Peptides, Regioselectivity, Tryptophan",

author = "Tank, {Disha Harsukhbhai} and Kharat, {Narendra Dinkar} and Kiran Bajaj and Panda, {Siva S.} and Rajeev Sakhuja",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = dec,

doi = "10.1002/ajoc.202300503",

language = "English (US)",

volume = "12",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "12",

}

TY - JOUR

T1 - Rhodium-Catalyzed Regioselective C7Ar-Functionalization of Tryptophan with Quinones and its Late Stage Peptide Exemplification

AU - Tank, Disha Harsukhbhai

AU - Kharat, Narendra Dinkar

AU - Bajaj, Kiran

AU - Panda, Siva S.

AU - Sakhuja, Rajeev

PY - 2023/12

Y1 - 2023/12

N2 - Pivaloyl-directed Rh(III)-catalyzed regioselective C7Ar-H functionalization of protected tryptophans were accomplished with 1,4-benzoquinones, furnishing a series of quinone-appended tryptophan-based unnatural amino acids in high yields. Further, the late stage functionalization on tryptophan-containing dipeptides was achieved with 1,4-benzoquinones in moderate reactivity.

AB - Pivaloyl-directed Rh(III)-catalyzed regioselective C7Ar-H functionalization of protected tryptophans were accomplished with 1,4-benzoquinones, furnishing a series of quinone-appended tryptophan-based unnatural amino acids in high yields. Further, the late stage functionalization on tryptophan-containing dipeptides was achieved with 1,4-benzoquinones in moderate reactivity.

KW - Functionalization

KW - Metal-Catalysis

KW - Peptides

KW - Regioselectivity

KW - Tryptophan

UR - http://www.scopus.com/inward/record.url?scp=85177739844&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85177739844&partnerID=8YFLogxK

U2 - 10.1002/ajoc.202300503

DO - 10.1002/ajoc.202300503

M3 - Article

AN - SCOPUS:85177739844

SN - 2193-5807

VL - 12

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 12

M1 - e202300503

ER -