Synthesis of the first α-fluoro-phosphotyrosyl mimetic

Zhen Dan Shi; Hongpeng Liu; Manchao Zhang; Dajun Yang; Terrence R. Burke

doi:10.1081/SCC-200034770

Synthesis of the first α-fluoro-phosphotyrosyl mimetic

Zhen Dan Shi, Hongpeng Liu, Manchao Zhang, Dajun Yang, Terrence R. Burke

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

7 Scopus citations

Abstract

The diastereoselective preparation of (2S)-2-fluoro-4-[[bis(1,1- dimethylethoxy)phosphinyl]methyl] benzenepropanoic acid (5) is presented as new phosphotyrosyl (pTyr) mimetic suitably protected for incorporation into peptides. Synthesis of 5 utilized electrophilic fluorination under chiral induction provided by the commercially available Evans auxiliary, (S)-(+)-4-phenyl-2-oxazolidinone. In order to demonstrate its synthetic utility, analogue 5 was employed to prepare a signal transduction-directed tripeptide. The design considerations for this peptide and its preliminary biological evaluation are included.

Original language	English (US)
Pages (from-to)	3883-3889
Number of pages	7
Journal	Synthetic Communications
Volume	34
Issue number	21
DOIs	https://doi.org/10.1081/SCC-200034770
State	Published - 2004

Keywords

Chiral induction
Enantioselective
Fluorination
Phosphotyrosyl mimetic

ASJC Scopus subject areas

Organic Chemistry

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10.1081/SCC-200034770

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title = "Synthesis of the first α-fluoro-phosphotyrosyl mimetic",

abstract = "The diastereoselective preparation of (2S)-2-fluoro-4-[[bis(1,1- dimethylethoxy)phosphinyl]methyl] benzenepropanoic acid (5) is presented as new phosphotyrosyl (pTyr) mimetic suitably protected for incorporation into peptides. Synthesis of 5 utilized electrophilic fluorination under chiral induction provided by the commercially available Evans auxiliary, (S)-(+)-4-phenyl-2-oxazolidinone. In order to demonstrate its synthetic utility, analogue 5 was employed to prepare a signal transduction-directed tripeptide. The design considerations for this peptide and its preliminary biological evaluation are included.",

keywords = "Chiral induction, Enantioselective, Fluorination, Phosphotyrosyl mimetic",

author = "Shi, {Zhen Dan} and Hongpeng Liu and Manchao Zhang and Dajun Yang and Burke, {Terrence R.}",

note = "Funding Information: 1Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute, National Institutes of Health, NCI-Frederick, Frederick, Maryland, USA 2Department of Hematology/Oncology, University of Michigan Medical School, Ann Arbor, Michigan, USA",

year = "2004",

doi = "10.1081/SCC-200034770",

language = "English (US)",

volume = "34",

pages = "3883--3889",

journal = "Synthetic Communications",

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publisher = "Taylor and Francis Ltd.",

number = "21",

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TY - JOUR

T1 - Synthesis of the first α-fluoro-phosphotyrosyl mimetic

AU - Shi, Zhen Dan

AU - Liu, Hongpeng

AU - Zhang, Manchao

AU - Yang, Dajun

AU - Burke, Terrence R.

N1 - Funding Information: 1Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute, National Institutes of Health, NCI-Frederick, Frederick, Maryland, USA 2Department of Hematology/Oncology, University of Michigan Medical School, Ann Arbor, Michigan, USA

PY - 2004

Y1 - 2004

N2 - The diastereoselective preparation of (2S)-2-fluoro-4-[[bis(1,1- dimethylethoxy)phosphinyl]methyl] benzenepropanoic acid (5) is presented as new phosphotyrosyl (pTyr) mimetic suitably protected for incorporation into peptides. Synthesis of 5 utilized electrophilic fluorination under chiral induction provided by the commercially available Evans auxiliary, (S)-(+)-4-phenyl-2-oxazolidinone. In order to demonstrate its synthetic utility, analogue 5 was employed to prepare a signal transduction-directed tripeptide. The design considerations for this peptide and its preliminary biological evaluation are included.

AB - The diastereoselective preparation of (2S)-2-fluoro-4-[[bis(1,1- dimethylethoxy)phosphinyl]methyl] benzenepropanoic acid (5) is presented as new phosphotyrosyl (pTyr) mimetic suitably protected for incorporation into peptides. Synthesis of 5 utilized electrophilic fluorination under chiral induction provided by the commercially available Evans auxiliary, (S)-(+)-4-phenyl-2-oxazolidinone. In order to demonstrate its synthetic utility, analogue 5 was employed to prepare a signal transduction-directed tripeptide. The design considerations for this peptide and its preliminary biological evaluation are included.

KW - Chiral induction

KW - Enantioselective

KW - Fluorination

KW - Phosphotyrosyl mimetic

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DO - 10.1081/SCC-200034770

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VL - 34

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EP - 3889

JO - Synthetic Communications

JF - Synthetic Communications

IS - 21

ER -

Synthesis of the first α-fluoro-phosphotyrosyl mimetic

Abstract

Keywords

ASJC Scopus subject areas

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