Modulation of reactivity in native chemical ligation through the use of thiol additives

Journal of the American Chemical Society

Volumn 119, Issue 19, 1997, Pages 4325-4329

  Dawson, Philip E ^a   Churchill, Michael J ^a   Ghadiri, M Reza ^a   Kent, Stephen B H ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ESTERIFICATION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; STRUCTURE ANALYSIS;

EID: 0030973396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962656r     Document Type: Article

References (26)

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16. 9 Although the product of this reaction has been described as a perthioester [(COSSNB) Liu, C. F.; Rao, C.; Tam, J. P. Tetrahedron Lett. 1996, 37, 933-936], in our hands, the peptide-α-thioester is the final reaction product under these conditions, as characterized by electrospray mass spectrometry (manuscript in preparation). It is important to note that the majority of peptide-α-thioesters used in this work have been synthesized by a different synthetic procedure, alkylation of peptide-α-thioacids, and therefore can be unambiguously characterized as thioesters.
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19. The barnase wild-type sequence is as follows: AQVINTFDGV. ADYLQTYHKL. PNDYITKSEA. QALGWVASKG. NLADVAPGKS. IGGDIFSNRE. GKLPGKSGRT. WREADINYTS. GFRNSDRILY. SSDWLIYKTT. DHYQTFTKIR. Hartley, R. W. J. Mol. Biol. 1988, 202, 913-915.
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