Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides

Abdul H. Fauq; Feng Hong; Bernadette Cusack; Beth M. Tyler; Yuan Ping-Pang; Elliott Richelson

doi:10.1016/S0957-4166(98)00445-5

Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides

Abdul H. Fauq, Feng Hong, Bernadette Cusack, Beth M. Tyler, Yuan Ping-Pang, Elliott Richelson

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

26 Scopus citations

Abstract

A convenient, multigram synthesis of a novel α-amino acid (2S)-2- amino-3-(1H-4-indolyl)propanoic acid (la), is reported. An Fmoc-t-Boc derivative of this novel regioisomer of the natural aromatic amino acid tryptophan could be readily incorporated into bioactive synthetic peptides using standard solid phase synthesis. The synthesis featured the use of Schollkopf chiral auxiliary reagents for chirality induction during a key step.

Original language	English (US)
Pages (from-to)	4127-4134
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	9
Issue number	23
DOIs	https://doi.org/10.1016/S0957-4166(98)00445-5
State	Published - Dec 11 1998

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides",

abstract = "A convenient, multigram synthesis of a novel α-amino acid (2S)-2- amino-3-(1H-4-indolyl)propanoic acid (la), is reported. An Fmoc-t-Boc derivative of this novel regioisomer of the natural aromatic amino acid tryptophan could be readily incorporated into bioactive synthetic peptides using standard solid phase synthesis. The synthesis featured the use of Schollkopf chiral auxiliary reagents for chirality induction during a key step.",

author = "Fauq, {Abdul H.} and Feng Hong and Bernadette Cusack and Tyler, {Beth M.} and Yuan Ping-Pang and Elliott Richelson",

note = "Funding Information: This work was supported by NIH (Grant no. MH27692, awarded to ER).",

year = "1998",

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T1 - Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides

AU - Fauq, Abdul H.

AU - Hong, Feng

AU - Cusack, Bernadette

AU - Tyler, Beth M.

AU - Ping-Pang, Yuan

AU - Richelson, Elliott

N1 - Funding Information: This work was supported by NIH (Grant no. MH27692, awarded to ER).

PY - 1998/12/11

Y1 - 1998/12/11

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AB - A convenient, multigram synthesis of a novel α-amino acid (2S)-2- amino-3-(1H-4-indolyl)propanoic acid (la), is reported. An Fmoc-t-Boc derivative of this novel regioisomer of the natural aromatic amino acid tryptophan could be readily incorporated into bioactive synthetic peptides using standard solid phase synthesis. The synthesis featured the use of Schollkopf chiral auxiliary reagents for chirality induction during a key step.

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Synthesis of (2S)-2-amino-3-(1H-4-indolyl)propanoic acid, a novel tryptophan analog for structural modification of bioactive peptides

Abstract

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