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SITE-SPECIFIC  11 C -LABELING OF PEPTIDES USING [ 11 C ]METHYLATING AGENTS By Erin Saucke-Lacelle, Esther Schirrmacher,  Dean Jolly, Ralf Schirrmacher
OBJECTIVE site-specific labeling of unprotected peptides using  11 C  methylating agents in one-step
ALREADY DONE ,[object Object],[object Object],Labelling agent: [ 11 C]Methoxy-benzaldehyde -Wester et. al, Munich, 2004
METHOD ,[object Object],[object Object],[object Object],[object Object],[ 11 C]Methyliodide [ 11 C]Methyltriflate [ 11 C]Methylnonaflate ,[object Object],[object Object]
Trp-Tyr-Phe-Phe-Lys-Gly 5 side chains 3 possibilities HPLC conditions: Agilent 1200 series multiwavelength UV, Raytest radioactivity detector, LiChrosorb column 250 x 10mm, flow 2.0 ml/min,  ACCN (0.05%TFA)/H2O (0.05% TFA), gradient from 100% H2O to 0% within 40 min
Trp-Tyr-Trp-Ser-Arg-Cys-Lys-Trp-Thr-Gly 9 side chains 7 possibilities HPLC conditions: Agilent 1200 series multiwavelength UV, Raytest radioactivity detector, Chromolith column 100 x 4.6mm, flow 1.4 ml/min,  H2O(0.05%TFA)/ ACCN(0.05% TFA), gradient from 100% H2O to 0% within 40 min
RESULTS-   Optimum reaction parameters ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[11C]Methyliodide [11C]Methyltriflate [11C]Methylnonaflate 6-mere DCM X N-terminal (2,3) n/a AcCN (6% H2O) X N-terminal (2,3), TYR (2,3) N-terminal (2,3), TYR (2,3) 10-mere DCM X X n/a AcCN (6% H2O) X CYS (3,4,5,6,7) X [11C]Methyliodide [11C]Methyltriflate [11C]Methylnonaflate 6-mere DCM X N-terminal (2,3) n/a AcCN (6% H2O) X N-terminal (2,3), TYR (2,3) N-terminal (2,3), TYR (2,3) 10-mere DCM X X n/a AcCN (6% H2O) X CYS (3,4,5,6,7) n/a
CONCLUSION ,[object Object],[object Object],[object Object],[object Object],[object Object]
ACKNOWLEDGEMENTS ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]

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C-11 Labeling of Peptides in a Single Step

  • 1. SITE-SPECIFIC 11 C -LABELING OF PEPTIDES USING [ 11 C ]METHYLATING AGENTS By Erin Saucke-Lacelle, Esther Schirrmacher, Dean Jolly, Ralf Schirrmacher
  • 2. OBJECTIVE site-specific labeling of unprotected peptides using 11 C methylating agents in one-step
  • 3.
  • 4.
  • 5. Trp-Tyr-Phe-Phe-Lys-Gly 5 side chains 3 possibilities HPLC conditions: Agilent 1200 series multiwavelength UV, Raytest radioactivity detector, LiChrosorb column 250 x 10mm, flow 2.0 ml/min, ACCN (0.05%TFA)/H2O (0.05% TFA), gradient from 100% H2O to 0% within 40 min
  • 6. Trp-Tyr-Trp-Ser-Arg-Cys-Lys-Trp-Thr-Gly 9 side chains 7 possibilities HPLC conditions: Agilent 1200 series multiwavelength UV, Raytest radioactivity detector, Chromolith column 100 x 4.6mm, flow 1.4 ml/min, H2O(0.05%TFA)/ ACCN(0.05% TFA), gradient from 100% H2O to 0% within 40 min
  • 7.
  • 8.
  • 9.

Hinweis der Redaktion

  1. *** write?: 11C-MeI *they say no mo than 5 words……. *7 words wide, 7 lines tall *white words on dark (blue, blk) bkgrnd
  2. * Is it possible to align all of the titles from all slides?
  3. Intro: just 1 ex of 11C-labeled peptide that exists?? Not as simple as our method…
  4. 5 (6?)side chains *remove C’s, just leave Os, S & Ns……
  5. X side chains, X possibilities, correct? *remove C’s, just leave Os, S & Ns……
  6. {total synthesis time EOB 25 min + work-up (5-7 min in DCM, 25-30 min in AcCN with HPLC)}