Synthesis of racemic [2′‐13C]tryptophan

B. R. Branchini; F. G. Prendergast; G. A. Spencer; J. D. Hugdahl; B. D. Ray; M. D. Kemple

doi:10.1002/jlcr.2580240605

Synthesis of racemic [2′‐¹³C]tryptophan

B. R. Branchini, F. G. Prendergast, G. A. Spencer, J. D. Hugdahl, B. D. Ray, M. D. Kemple

Pharmacology

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

4 Scopus citations

Abstract

[2‐¹³C] Indole was synthesized in 39% yield by a three‐step procedure starting with K¹³CN. The labeled indole was converted to D,L[2′‐¹³C] tryptophan in three subsequent steps and the overall yield from K¹³CN was 13.5%. Proton and ¹³C‐NMR, and GC/mass spectral analyses confirmed the position and extent of ¹³C incorporation.

Original language	English (US)
Pages (from-to)	637-643
Number of pages	7
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	24
Issue number	6
DOIs	https://doi.org/10.1002/jlcr.2580240605
State	Published - Jun 1987

Keywords

D, L‐[2′‐C]tryptophan
[2‐C] indole
indole synthesis
tryptophan synthesis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

Access to Document

10.1002/jlcr.2580240605

Cite this

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title = "Synthesis of racemic [2′‐13C]tryptophan",

abstract = "[2‐13C] Indole was synthesized in 39% yield by a three‐step procedure starting with K13CN. The labeled indole was converted to D,L[2′‐13C] tryptophan in three subsequent steps and the overall yield from K13CN was 13.5%. Proton and 13C‐NMR, and GC/mass spectral analyses confirmed the position and extent of 13C incorporation.",

keywords = "D, L‐[2′‐C]tryptophan, [2‐C] indole, indole synthesis, tryptophan synthesis",

author = "Branchini, {B. R.} and Prendergast, {F. G.} and Spencer, {G. A.} and Hugdahl, {J. D.} and Ray, {B. D.} and Kemple, {M. D.}",

year = "1987",

month = jun,

doi = "10.1002/jlcr.2580240605",

language = "English (US)",

volume = "24",

pages = "637--643",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

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T1 - Synthesis of racemic [2′‐13C]tryptophan

AU - Branchini, B. R.

AU - Prendergast, F. G.

AU - Spencer, G. A.

AU - Hugdahl, J. D.

AU - Ray, B. D.

AU - Kemple, M. D.

PY - 1987/6

Y1 - 1987/6

N2 - [2‐13C] Indole was synthesized in 39% yield by a three‐step procedure starting with K13CN. The labeled indole was converted to D,L[2′‐13C] tryptophan in three subsequent steps and the overall yield from K13CN was 13.5%. Proton and 13C‐NMR, and GC/mass spectral analyses confirmed the position and extent of 13C incorporation.

AB - [2‐13C] Indole was synthesized in 39% yield by a three‐step procedure starting with K13CN. The labeled indole was converted to D,L[2′‐13C] tryptophan in three subsequent steps and the overall yield from K13CN was 13.5%. Proton and 13C‐NMR, and GC/mass spectral analyses confirmed the position and extent of 13C incorporation.

KW - D, L‐[2′‐C]tryptophan

KW - [2‐C] indole

KW - indole synthesis

KW - tryptophan synthesis

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DO - 10.1002/jlcr.2580240605

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JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

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