Direct reductive alkylation of amino acids: Synthesis of bifunctional chelates for nuclear imaging

Synthesis

Volumn , Issue 11, 2004, Pages 1759-1766

  Levadala, Murali K ^a   Banerjee, Sangeeta Ray ^a   Maresca, Kevin P ^b   Babich, John W ^b   Zubieta, Jon ^a  

^a SYRACUSE UNIVERSITY   (United States)

^b A Subsidiary of Lantheus Holdings   (United States)

Author keywords

Amino acids; Bifunctional chelators; Radiopharmaceuticals; Reductive alkylation; Sodium triacetoxyborohydride

Indexed keywords

ALDEHYDES; AMINO ACIDS; CHELATION; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

CHELATORS; RADIOPHARMACEUTICALS;

ALKYLATION;

2 (TERT BUTOXYCARBONYL)AMINO 6 [(PYRIDIN 2 YL)METHYL]AMINO 1 HEXANOIC ACID; 2 (TERT BUTOXYCARBONYL)AMINO 6 [[(1 METHYL 1H IMIDAZOL 2 YL)METHYL][(PYRIDIN 2 YL)METHYL]]AMINO 1 HEXANOIC ACID; 2 (TERT BUTOXYCARBONYL)AMINO 6 [[(PYRIDIN 2 YL)METHYL][(THIAZOL 2 YL)METHYL]]AMINO 1 HEXANOIC ACID; 2 [BIS(PYRIDIN 2 YL)METHYL]AMINO 1 ETHANOIC ACID; 2 [BIS(PYRIDIN 2 YL)METHYL]AMINO 3 PHENYL 1 PROPIONIC ACID; 2 [BIS(PYRIDIN 2 YL)METHYL]AMINO 6 (TERT BUTOXYCARBONYL)AMINO 1 HEXANOIC ACID; 2,6 [BIS(PYRIDIN 2 YL)METHYL]DIAMINO 1 HEXANOIC ACID; 5 [(PYRIDIN 2 YL)METHYL]AMINO 1 PENTANOIC ACID; 5 [BIS(PYRIDIN 2 YL)METHYL]AMINO 1 PENTANOIC ACID; 6 DIBENZYLAMINO 2 (9H FLUOREN 9 YLMETHOXYCARBONYL)AMINO 1 HEXANOIC ACID; 6 [BIS(1 METHYL 1H IMIDAZOL 2 YL)METHYL]AMINO 2 (9H FLUOREN 9 YLMETHOXYCARBONYL)AMINO 1 HEXANOIC ACID; 6 [BIS(PYRIDIN 2 YL)METHYL]AMINO 2 (9H FLUOREN 9 YLMETHOXYCARBONYL)AMINO 1 HEXANOIC ACID; 6 [BIS(QUINOLIN 2 YL)METHYL]AMINO 2 (9H FLUOREN 9 YLMETHOXYCARBONYL)AMINO 1 HEXANOIC ACID; 6 [BIS(TERT BUTOXYCARBONYLMETHYLAMINO)] 2 (9H FLUOREN 9 YLMETHOXYCARBONYLAMINO)HEXANOIC ACID; 6 [BIS(THIAZOL 2 YL)METHYL]AMINO 2 (9H FLUOREN 9 YLMETHOXYCARBONYL)AMINO 1 HEXANOIC ACID; 6 [[(TERT BUTOXYCARBONYL)METHYL][(PYRIDIN 2 YL)METHYL]]AMINO 2 (9H FLUOREN 9 YLMETHOXYCARBONYL]AMINO 1 HEXANOIC ACID; ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; CHELATING AGENT; RADIOPHARMACEUTICAL AGENT; REAGENT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; SCINTISCANNING; STRUCTURE ANALYSIS;

EID: 4043130469     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829120     Document Type: Article

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14. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
15. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
16. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
17. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
18. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
19. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
20. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
21. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
22. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
23. 3 = mercaptoacetylglycylglycylglycine): Liu, S.; Edwards, D. S.; Looby, R. J.; Poirier, M. J.; Rajopadhye, M.; Bourque, J. P.; Carroll, T. R. Bioconjugate Chem. 1996, 7, 196. (b) See also: Kasina, S.; Sanderson, J. A.; Fitzner, J. N.; Srinivasan, A.; Rao, T. N.; Hobson, L. J.; Reno, J. M.; Axworthy, D. B.; Beaumier, P. L.; Fritzberg, A. R. Bioconjugate Chem. 1998, 9, 108. (c) See also: Van Domselaar, G. H.; Okarvi, S. M.; Fanta, M.; Suresh, M. R.; Wishart, D. S. J. Labelled Comp. Radiopharm. 2000, 43, 1193. (d) See also: Zhu, Z.; Wang, Y.; Zhang, Y.; Liu, G.; Liu, N.; Rusckowski, M.; Hnatowich, D. J. Nucl. Med. Biol. 2001, 28, 703; and references therein. (e) Other cysteine-containing tripeptides and derivatives: Goodbody, A.; Pollak, A. WO Patent Appl. 9522996, 1995; Chem. Abstr. 1995, 123, 250205. (f) See also: Pollak, A.; Goodbody, A. E.; Ballinger, J. R.; Duncan, G. S.; Tran, L. L.; Dunn-Dufault, R.; Meghji, K.; Lau, F.; Andrey, T. W. Nucl. Med. Commun. 1996, 17, 132. (g) See also: Lister-James, J.; Knight, L. C.; Mauer, A. H.; Bush, L. R.; Moyer, B. R.; Dean, R. T. J. Nucl. Med. 1996, 37, 775. (h) See also: Pearson, D. A.; Lister-James, J.; McBride, W. J.; Wilson, D. M.; Martel, L. J.; Civitello, E. R.; Taylor, J. E.; Moyer, B. R.; Dean, R. T. J. Med. Chem. 1996, 39, 1361. (i) See also: Wishart, D. S. Tools for Protein Technologies, Biotechnology, 2nd ed., Vol. 5b; John Wiley & Sons: New York, 2001, 325. (j) Gly-Ala-Gly-Gly peptide: Ben-Haim, S.; Kahn, D.; Weiner, G. J.; Madsen, M. T.; Waxman, A. D.; Williams, C. M.; Clarke-Pearson, D. L.; Colemann, R. E.; Maguire, R. T. Nucl. Med. Biol. 1994, 21, 131. (k) Luyt, L. G.; Hunter, D. H. Book of Abstracts, 217th National Meeting of the American Chemical Society, Anaheim, CA, March 21-25: 1999; American Chemical Society: Washington DC, 1999, NUCL-184.
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