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Synthesis of N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate: a radio-iodination agent for labeling internalizing proteins and peptides.

Publication ,  Journal Article
Vaidyanathan, G; Zalutsky, MR
Published in: Nat Protoc
2007

This protocol describes a detailed procedure for the synthesis of N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate ([*I]SGMIB), an agent useful in the radio-iodination of proteins, including monoclonal Abs, and peptides that undergo internalization after receptor or antigen binding. In this procedure, the tin precursor N-succinimidyl 4-[N1,N2-bis(tert-butyloxycarbonyl)guanidinomethyl]-3-(trimethylstannyl)benzoate (Boc-SGMTB, 3) was first radio-iodinated to [*I]Boc-SGMIB, a derivative of [*I]SGMIB with the guanidine function protected with Boc groups. Treatment of [*I]Boc-SGMIB with trifluoroacetic acid delivered the final product. The total time for the synthesis and purification of [*I]Boc-SGMIB and its subsequent de-protection is approximately 140 min.

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Published In

Nat Protoc

DOI

EISSN

1750-2799

Publication Date

2007

Volume

2

Issue

2

Start / End Page

282 / 286

Location

England

Related Subject Headings

  • Staining and Labeling
  • Proteins
  • Molecular Structure
  • Guanidine
  • Chromatography, High Pressure Liquid
  • Bioinformatics
  • Benzoates
  • 11 Medical and Health Sciences
  • 06 Biological Sciences
  • 03 Chemical Sciences
 

Citation

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Vaidyanathan, G., & Zalutsky, M. R. (2007). Synthesis of N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate: a radio-iodination agent for labeling internalizing proteins and peptides. Nat Protoc, 2(2), 282–286. https://doi.org/10.1038/nprot.2007.20
Vaidyanathan, Ganesan, and Michael R. Zalutsky. “Synthesis of N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate: a radio-iodination agent for labeling internalizing proteins and peptides.Nat Protoc 2, no. 2 (2007): 282–86. https://doi.org/10.1038/nprot.2007.20.
Vaidyanathan, Ganesan, and Michael R. Zalutsky. “Synthesis of N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate: a radio-iodination agent for labeling internalizing proteins and peptides.Nat Protoc, vol. 2, no. 2, 2007, pp. 282–86. Pubmed, doi:10.1038/nprot.2007.20.

Published In

Nat Protoc

DOI

EISSN

1750-2799

Publication Date

2007

Volume

2

Issue

2

Start / End Page

282 / 286

Location

England

Related Subject Headings

  • Staining and Labeling
  • Proteins
  • Molecular Structure
  • Guanidine
  • Chromatography, High Pressure Liquid
  • Bioinformatics
  • Benzoates
  • 11 Medical and Health Sciences
  • 06 Biological Sciences
  • 03 Chemical Sciences