Ninhydrin as a reversible protecting group of amino-terminal cysteine

Journal of Peptide Research

Volumn 63, Issue 3, 2004, Pages 223-234

  Pool, C T ^a   Boyd, J G ^b   Tam, J P ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b PFIZER INC   (United States)

Author keywords

His(Bom); Ninhydrin; NT cysteine; Peptide; Reversible protecting group; Thiazolidine

Indexed keywords

AMINE; CYSTEINE; FUNCTIONAL GROUP; HISTIDINE DERIVATIVE; HYDROFLUORIC ACID; NINHYDRIN; RESIN; THIAZOLE DERIVATIVE; THIOL GROUP; TRIFLUOROACETIC ACID;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DEPROTECTION REACTION; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN STABILITY; REDUCTION;

CYSTEINE; MOLECULAR STRUCTURE; NINHYDRIN; PEPTIDES, CYCLIC;

EID: 1942502335     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2004.00127.x     Document Type: Article

References (50)

1. Tam, J.P., Yu, Q. & Miao, Z. (1999) Orthogonal ligation strategies for peptide and protein. Biopolymers 51, 311-332.
2. Tam, J.P., Lu, Y.A., Liu, C.F. & Shao, J. (1995) Peptide synthesis using unprotected peptides through orthogonal coupling methods. Proc. Natl. Acad. Sci. 92, 12485-12489.
3. Dawson, P.E., Churchill, M., Ghadiri, M.R. & Kent, S.B.H. (1997) Modulation of reactivity in native chemical ligation through the use of thiol additives. J. Am. Chem. Soc. 119, 4325-4329.
4. Lu, W., Qasim, M.A. & Kent, S.B.H. (1996) Comparative total syntheses of Turkey ovomucoid third domain by both stepwise solid phase peptide synthesis and native chemical ligation. J. Am. Chem. Soc. 118, 8518-8523.
5. Camarero, J.A., Cotton, G.J., Adeva, A. & Muir, T.W. (1998) Chemical ligation of unprotected peptides directly from a solid support. J. Peptide Res. 51, 303-316.
6. Beligere, G.S. & Dawson, P.E. (1999) Conformationally assisted protein ligation using C-terminal thioester peptides. J. Am. Chem. Soc. 121, 6332-6333.
7. Tam, J.P. & Lu, Y.A. (1998) A biomimetic strategy in the synthesis and fragmentation of cyclic protein. Protein Sci. 7, 1583-1592.
8. Tam, J.P., Lu, Y.A. & Yu, Q. (1999) Thia Zip reaction for synthesis of large cyclic peptides: mechanisms and applications. J. Am. Chem. Soc. 121, 4316-4324.
9. Zhang, L. & Tam, J.P. (1997) Synthesis and application of unprotected cyclic peptides as building blocks for peptide dendrimers. J. Am. Chem. Soc. 119, 2363-2370.
10. Shao, Y., Lu, W. & Kent, S.B.H. (1998) A novel method to synthesize cyclic peptides. Tetrahedron Lett. 39, 3911-3914.
11. Camarero, J.A. & Muir, T.W. (1997) Chemoselective backbone cyclization of unprotected peptides. Chem. Comm. (Cambridge) 15, 1369-1370.
12. Camarero, J.A. & Muir, T.W. (1999) Biosynthesis of a head-to-tail cyclized protein with improved biological activity. J. Am. Chem. Soc. 121, 5597-5598.
13. Camarero, J.A., Pavel, J. & Muir, T.W. (1998) Chemical synthesis of a circular protein domain: evidence for folding-assisted cyclization. Angew. Chem., Int. Ed. 37, 347-349.
14. Liu, C.F. & Tam, J.P. (1994) Peptide segment ligation strategy without use of protecting groups. Proc. Natl. Acad. Sci. 91, 6584-6588.
15. Tam, J.P. & Miao, Z. (1999) Stereo specific pseudoproline ligation of N-terminal serine, threonine, or cysteine-containing unprotected peptides. J. Am. Chem. Soc. 121, 9013-9022.
16. Zhang, L. & Tam, J.P. (1996) Thiazolidine formation as a general and site-specific conjugation method for synthetic peptides and proteins. Anal. Biochem. 233, 87-93.
17. Botti, P., Pallin, T.D. & Tam, J.P. (1996) Cyclic peptides from linear unprotected peptide precursors through thiazolidine formation. J. Am. Chem. Soc. 118, 10018-10024.
18. Spetzler, J.C. & Tam, J.P. (1996) Self-assembly of cyclic peptides on a dendrimer: multiple cyclic antigen peptides. Pept. Res. 9, 290-296.
19. Evans, T.C. Jr & Xu, M.Q. (2000) Inteinmediated protein ligation: harnessing nature's escape artists. Biopolymers 51, 333-342.
20. Cotton, G.J. & Muir, T.W. (1999) Peptide ligation and its application to protein engineering. Chem. Biol. 6, 247-256.
21. Chong, S., Mersha, F.B., Comb, D.G., Scott, M.E., Landry, D., Vence, L.M., Perler, F.B., Benner, J., Kucera, R.B., Hirvonen, C.A., Pelletier, J.J., Paulus, H. & Xu, M.Q. (1997) Single-column purification of free recombinant proteins using a self-cleavable affinity tag derived from a protein splicing element. Gene 192, 271-281.
22. Muir, T.W., Sondhi, D. & Cole, P.A. (1998) Expressed protein ligation: a general method for protein engineering. Proc. Natl. Acad. Sci. 95, 6705-6710.
23. Cotton, G.J., Ayers, B., Xu, R. & Muir, T.W. (1999) Insertion of a synthetic peptide into a recombinant protein framework: a protein biosensor. J. Am. Chem. Soc. 121, 1100-1101.
24. Ayers, B., Blaschke, U.K., Camarero, J.A., Cotton, G.J., Holford, M. & Muir, T.W. (2000) Introduction of unnatural amino acids into proteins using expressed protein ligation. Biopolymers 51, 343-354.
25. Severinov, K. & Muir, T.W. (1998) Expressed protein ligation, a novel method for studying protein-protein interaction in transcription. J. Biol. Chem. 273, 16205-16209.
26. Evans, T.C. Jr, Benner, J. & Xu, M.Q. (1999) The in vitro ligation of bacterially expressed proteins using an intein from Methanobacterium thermoautotrophicum. J. Biol. Chem. 274, 3923-3926.
27. Evans, T.C. Jr, Benner, J. & Xu, M.Q. (1999) The cyclization and polymerization of bacterially expressed proteins using modified self-splicing inteins. J. Biol. Chem. 274, 18359-18363.
28. Xu, R., Ayers, B., Cowburn, D. & Muir, T.W. (1999) Chemical ligation of folded recombinant proteins: segmental isotopic labeling of domains for NMR studies. Proc. Natl. Acad. Sci. 96, 388-393.
29. Williams, K.P., Rayhorn, P., Chi-Rosso, G., Garber, E.A., Strauch, K.L., Horan, G.S.B., Reilly, J.O., Baker, D.P., Taylor, F.R., Koteliansky, V. & Pepinsky, R.B. (1999) Functional antagonists of sonic hedgehog reveal the importance of the N terminus for activity. J. Cell Sci. 112, 4405-4414.
30. Pepinsky, R.B., Zeng, C., Wen, D., Rayhorn, P., Baker, D.P., Williams, K.P., Bixler, S.A., Ambrose, C.M., Garber, E.A., Miatkowski, K., Taylor, F.R., Wang, E.A. & Galdes, A. (1998) Identification of a palmitic acid-modified form of human Sonic hedgehog. J. Biol. Chem. 273, 14037-14045.
31. Kotake, H., Agellon, L.B. & Yokoyama, S. (1997) Modification of the N-terminal cysteine of plasma cholesteryl ester transfer protein selectively inhibits triglyceride transfer activity. Biochim. Biophys. Acta. 1347, 69-74.
32. Kallen, R.G. (1971) The mechanism of reactions involving Schiff base intermediates. Thiazolidine formation from L-cysteine and formaldehyde. J. Am. Chem. Soc. 93, 6236-6248.
33. Mitchell, M.A., Runge, T.A., Mathews, W.R., Ichhpurani, A.K., Harn, N.K., Dobrowolski, P.J. & Eckenrode, F.M. (1990) Problems associated with use of the benzyloxymethyl protecting group for histidines. Formaldehyde adducts formed during cleavage by hydrogen fluoride. Int. J. Peptide & Protein Res. 36, 350-355.
34. Kumagaye, K.Y., Inui, T., Nakajima, K., Kimura, T. & Sakakibara, S. (1991) Suppression of a side reaction associated with N(im)-benzyloxymethyl group during synthesis of peptides containing cysteinyl residue at the N-terminus. Peptide Res. 4, 84-87.
35. Moore, S. & Stein, W.H. (1948) Photometric ninhydrin method for use in the chromatography of amino acids. J. Biol. Chem. 176, 367-372.
36. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34, 595-598.
37. Sarin, V.K., Kent, S.B.H., Tam, J.P. & Merrifield, R.B. (1981) Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction. Anal. Biochem. 117, 147-157.
38. Friedman, M. & Sigel, C.W. (1966) A kinetic study of the ninhydrin reaction. Biochemistry 5, 478-485.
39. Prota, G. & Ponsiglione, E. (1973) On the reaction of ninhydrin with cysteine and its analogues: a revision. Tetrahedron 29, 4271-4274.
40. Kuhn, R. & Hammer, I. (1951) Reaction products of quinones and other carbonyl compounds with cysteine. Chem. Ber. 84, 91-95.
41. Schoenberg, A., Singer, E., Eschenhof, B. & Hoyer, G.A. (1978) 1,2,3-Tricarbonyl compounds, XIII. Reaction of ninhydrin and of 1,2,3-indantrione with compounds with two functional groups. A contribution to the formation of spiro compounds from ninhydrin. Chem. Ber. 111, 3058-3067.
42. Woodward, R.B. (1966) Recent advances in the chemistry of natural products. Science 153, 487-493.
43. Kemp, D.S. & Carey, R.I. (1989) Boc-L-Dmt-OH as a fully N,S-blocked cysteine derivative for peptide synthesis by prior thiol capture. Facile conversion of N-terminal Boc-L-Dmt-peptides to H-Cys(Scm)-peptides. J. Org. Chem. 54, 3640-3646.
44. Tam, J.P., Lu, Y.A., Liu, C.F. & Shao, J. (1995) Peptide synthesis using unprotected peptides through orthogonal coupling methods. Proc. Natl. Acad. Sci. 92, 12485-12489.
45. Friedman, M., Cavins, J. & Wall, J. (1965) Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α,β-unsaturated compounds. J. Am. Chem. Soc. 87, 3672-3682.
46. Riddles, P.W., Blakeley, R.L. & Zerner, B. (1983) Reassessment of Ellman's reagent. Meth. Enzymology 91, 49-60.
47. Pipkorn, R. & Ekberg, B. (1986) Histidine racemization in the synthesis of an analog of the luteinizing hormone releasing factor. Investigation by HPLC and enzymatic methods. Int. J. Peptide & Protein Res. 27, 583-588.
48. Clippingdale, A.B., Barrow, C.J. & Wade, J.D. (2000) Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation. J. Peptide Sci. 6, 225-234.
49. Ingenito, R., Bianchi, E., Fattori, D. & Pessi, A. (1999) Solid phase synthesis of peptide C-terminal thioesters by Fmoc/t-Bu chemistry. J. Am. Chem. Soc. 121, 11369-11374.
50. Schnolzer, M., Alewood, P., Jones, A., Alewood, D. & Kent, S.B. (1999) In situ neutralization in Boc-chemistry solid phase peptide synthesis. Rapid, high yield assembly of difficult sequences. Int. J. Peptide & Protein Res. 40, 180-193.