Synthesis of racemic [2′‐13C]tryptophan

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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)637-643
Number of pages7
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume24
Issue number6
DOIs
StatePublished - 1987

Fingerprint

Tryptophan
Protons
indole

Keywords

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

ASJC Scopus subject areas

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

Cite this

Branchini, B. R., Prendergast, F. G., Spencer, G. A., Hugdahl, J. D., Ray, B. D., & Kemple, M. D. (1987). Synthesis of racemic [2′‐13C]tryptophan. Journal of Labelled Compounds and Radiopharmaceuticals, 24(6), 637-643. https://doi.org/10.1002/jlcr.2580240605

Synthesis of racemic [2′‐13C]tryptophan. / Branchini, B. R.; Prendergast, F. G.; Spencer, G. A.; Hugdahl, J. D.; Ray, B. D.; Kemple, M. D.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 24, No. 6, 1987, p. 637-643.

Research output: Contribution to journalArticle

Branchini, BR, Prendergast, FG, Spencer, GA, Hugdahl, JD, Ray, BD & Kemple, MD 1987, 'Synthesis of racemic [2′‐13C]tryptophan', Journal of Labelled Compounds and Radiopharmaceuticals, vol. 24, no. 6, pp. 637-643. https://doi.org/10.1002/jlcr.2580240605
Branchini BR, Prendergast FG, Spencer GA, Hugdahl JD, Ray BD, Kemple MD. Synthesis of racemic [2′‐13C]tryptophan. Journal of Labelled Compounds and Radiopharmaceuticals. 1987;24(6):637-643. https://doi.org/10.1002/jlcr.2580240605
Branchini, B. R. ; Prendergast, F. G. ; Spencer, G. A. ; Hugdahl, J. D. ; Ray, B. D. ; Kemple, M. D. / Synthesis of racemic [2′‐13C]tryptophan. In: Journal of Labelled Compounds and Radiopharmaceuticals. 1987 ; Vol. 24, No. 6. pp. 637-643.
@article{79e7c49ff02c4886b9325373973e11e3,
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, indole synthesis, tryptophan synthesis, [2‐C] indole",
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",
doi = "10.1002/jlcr.2580240605",
language = "English (US)",
volume = "24",
pages = "637--643",
journal = "Journal of Labelled Compounds and Radiopharmaceuticals",
issn = "0362-4803",
publisher = "John Wiley and Sons Ltd",
number = "6",

}

TY - JOUR

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

Y1 - 1987

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 - indole synthesis

KW - tryptophan synthesis

KW - [2‐C] indole

UR - http://www.scopus.com/inward/record.url?scp=0023278222&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023278222&partnerID=8YFLogxK

U2 - 10.1002/jlcr.2580240605

DO - 10.1002/jlcr.2580240605

M3 - Article

VL - 24

SP - 637

EP - 643

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

SN - 0362-4803

IS - 6

ER -