Andersson C, Edlund PO, Gellerfors P, Hansson Y, Holmberg E, Hult C, Johansson S, Kördel J, Lundin R, Mendel-Hartvig I, Norén B, Wehler T, Widmalm G, Öhman J (1996) Isolation and characterization of a trisulfide variant of recombinant human growth hormone formed during expression in Escherichia coli. Int J Pept Prot Res 47:311–321. https://doi.org/10.1111/j.1399-3011.1996.tb01360.x
Andreu D, Albericio F, Solé NA, Munson MC, Ferrer M, Barany G (1994) Formation of disulfide bonds in synthetic peptides and proteins. In: Pennington MW, Dunn BM (eds) Methods in Molecular Biology, vol 35. Humana Press, Totowa, pp 91–169. https://doi.org/10.1385/0-89603-273-6:91
Annis I, Hargittai B, Barany G (1997) Disulfide bond formation. In: Fields GB (ed) Solid-phase peptide synthesis. Meth Enzymol 289:198–221. https://doi.org/10.1016/s0076-6879(97)89049-0
Barany G, Mott AW (1984) Chemistry of bis(alkoxycarbonyl)polysulfanes and related compounds. J Org Chem 49:1043–1051. https://doi.org/10.1021/jo00180a018
Barany G, Schroll AL, Mott AW, Halsrud DA (1983) A general strategy for elaboration of the dithiocarbonyl functionality, –(C=O)SS–: application to the synthesis of bis(chlorocarbonyl)disulfane and related derivatives of thiocarbonic acids. J Org Chem 48:4750–4761. https://doi.org/10.1021/jo00172a056
Böhme H, Brinkmann M, Steudel H-P (1981) Gewinnung und umsetzungen von chlordisulfanylderivaten der kohlensäure. Liebigs Ann Chem 1981:1244–1251. https://doi.org/10.1002/jlac.198119810711
Brois SJ, Pilot JF, Barnum HW (1970) New synthetic concepts in organosulfur chemistry. I. New pathway to unsymmetrical disulfides. The thiol-induced fragmentation of sulfenyl thiocarbonates. J Am Chem Soc 92:7629–7631. https://doi.org/10.1021/ja00729a042
Canova-Davis E, Baldonado IP, Chloupek RC, Ling VT, Gehant R, Olson K, Gillece-Castro BL (1996) Confirmation by mass spectrometry of a trisulfide variant in methionyl human growth hormone biosynthesized in Escherichia coli. Anal Chem 68:4044–4051. https://doi.org/10.1021/ac9605915
Article CAS PubMed Google Scholar
Chen L, Barany G (1996) N-dithiasuccinoyl (Dts)-glycine: a novel oxidation reagent for the formation of intramolecular disulfide bridges under mild conditions. Lett Pept Sci 3:283–292. https://doi.org/10.1007/bf00127662
Chen L, Zoulíková I, Slaninová J, Barany G (1997) Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: directed methods for the construction of disulfide and trisulfide bridges in peptides. J Med Chem 40:864–876. https://doi.org/10.1021/jm9607156
Article CAS PubMed Google Scholar
Chen L, Skinner SR, Gordon TD, Taylor JE, Barany G, Morgan BA (1999) Isolation, characterization and synthesis of a trisulfide related to the somatostatin analog lanreotide. In: Tam JP, Kaumaya PTP (eds) Peptides—Frontiers of Peptide Science: Proceedings of the Fifteenth American Peptide Symposium. Kluwer Academic Publishers, Dordrecht, pp 275–276. https://doi.org/10.1007/0-306-46862-X_114
du Vigneaud V (1956) Trail of sulfur research: from insulin to oxytocin. Science 123:967–974. https://doi.org/10.1126/science.123.3205.967
du Vigneaud V (1964) A trail of sulfur research: from insulin to oxytocin (Nobel Lecture, December 12, 1955). Nobel lectures–chemistry–including presentation speeches and laureates’ biographies, 1942–1962. Elsevier, Amsterdam, pp 446–465. https://www.nobelprize.org/uploads/2018/06/vigneaud-lecture.pdf
du Vigneaud V, Ressler C, Swan JM, Roberts CW, Katsoyannis PG, Gordon S (1953) The synthesis of an octapeptide amide with the hormonal activity of oxytocin. J Am Chem Soc 75:4879–4880. https://doi.org/10.1021/ja01115a553
Erlanson DA, Wells JA (1998) Facile synthesis of cyclic peptides containing di-, tri-, tetra-, and pentasulfides. Tetrahedron Lett 39:6799–6802. https://doi.org/10.1016/s0040-4039(98)01461-0
Fabio K, Curley K, Guarneri J, Adamo B, Laurenzi B, Grant M, Offord R, Kraft K, Leone-Bay A (2015) Heat-stable dry powder oxytocin formulations for delivery by oral inhalation. AAPS PharmSciTech 16:1299–1306. https://doi.org/10.1208/s12249-015-0314-0
Article CAS PubMed PubMed Central Google Scholar
Goerdeler J, Nandi K (1975) Über thioacyl-isocyanate, XI. Verfahren zu ihrer herstellung aus dithiazolonen. Chem Ber 108:3066–3070. https://doi.org/10.1002/cber.19751080926
Goerdeler J, Tiedt M-L, Nandi K (1981) Über thioacyl-isocyanate, XV. Reaktionen mit nucleophilen C‐verbindungen. Chem Ber 114:2713–2722. https://doi.org/10.1002/cber.19811140805
Góngora-Benítez M, Tulla-Puche J, Albericio F (2014) Multifaceted roles of Disulfide Bonds. Peptides as therapeutics. Chem Rev 114:901–926. https://doi.org/10.1021/cr400031z
Article CAS PubMed Google Scholar
Gu S, Wen D, Weinreb PH, Sun Y, Zhang L, Foley SF, Kshirsagar R, Evans D, Mi S, Meier W, Pepinsky RB (2010) Characterization of trisulfide modification in antibodies. Anal Biochem 400:89–98. https://doi.org/10.1016/j.ab.2010.01.019
Article CAS PubMed Google Scholar
Hawe A, Poole R, Romeijn S, Kasper P, van der Heijden R, Jiskoot W (2009) Towards heat-stable oxytocin formulations: analysis of degradation kinetics and identification of degradation products. Pharm Res 26:1679–1688. https://doi.org/10.1007/s11095-009-9878-2
Article CAS PubMed PubMed Central Google Scholar
Henley MJ, Schroll AL, Young VG, Barany G (2015) Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane. Acta Crystallogr E Cryst Commun 71:1371–1374. https://doi.org/10.1107/S2056989015018289
Hiskey RG, Muthukumaraswamy N, Vunnam RR (1975) Sulfur-containing polypeptides XVII. The S-carbomethoxysulfenyl derivative as a protective group for cysteine. J Org Chem 40:950–953. https://doi.org/10.1021/jo00895a600
Article CAS PubMed Google Scholar
Kaiser E, Colescott RL, Bossinger CD, Cook PI (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal Biochem 34:595–598. https://doi.org/10.1016/0003-2697(70)90146-6
Article CAS PubMed Google Scholar
Kamber B (1973) Die gezielte synthese offenkettiger asymmetrischer cystinpeptide mittels thiol-induzierter fragmentierung von sulfenylthiocarbonanten. Insulinfragmente mit intakter disulfidbrücke A20-B19. Helv Chim Acta 56:1370–1381. https://doi.org/10.1002/hlca.19730560420
Article CAS PubMed Google Scholar
Kshirsagar R, McElearney K, Gilbert A, Sinacore M, Ryll T (2012) Controlling trisulfide modification in recombinant monoclonal antibody produced in fed-batch cell culture. Biotech Bioengin 109:2523–2532. https://doi.org/10.1002/bit.24511
Lau JL, Dunn MK (2018) Therapeutic peptides: historical perspectives, current development trends, and future directions. Bioorg Med Chem 26:2700–2707. https://doi.org/10.1016/j.bmc.2017.06.052
Article CAS PubMed Google Scholar
Lindahl S, Xian M (2023) Recent development of polysulfides: chemistry and biological applications. Curr Opin Chem Biol 75:e102325. https://doi.org/10.1016/j.cbpa.2023.102325
Lundin RHL, Norén BE, Olof Edlund P (1994) A convenient method for the synthesis of peptide trisulfides. Tetrahedron Lett 35:6339–6342. https://doi.org/10.1016/S0040-4039(00)73427-7
Magon N, Kalra S (2011) The orgasmic history of oxytocin: love, lust, and labor. Indian J Endocr Metab 15:S156–S161. https://doi.org/10.4103/2230-8210.84851
Malm M, Madsen I, Kjellström J (2018) Development and stability of a heat-stable formulation of carbetocin for the prevention of postpartum haemorrhage for use in low and middle-income countries. J Pep Sci 24:e3082. https://doi.org/10.1002/psc.3082
Manning M, Misicka A, Olma A, Bankowski K, Stoev S, Chini B, Durroux T, Mouillac B, Corbani M, Guillon G (2012) Oxytocin and vasopressin agonists and antagonists as research tools and potential therapeutics. J Neuroendocrinol 24:609–628. https://doi.org/10.1111/j.1365-2826.2012.02303.x
Article CAS PubMed PubMed Central Google Scholar
Mott AW, Barany G (1984) A new method for the synthesis of unsymmetrical trisulfanes. Synthesis. https://doi.org/10.1055/s-1984-30922
Mott AW, Słomczyñska U, Barany G (1986) Formation of sulfur-sulfur bonds during solid-phase peptide synthesis: application to the synthesis of oxytocin. In: Castro B, Martinez J (eds) Forum Peptides Le Cap d’Agde 1984. Les Impressions Dohr, Nancy, pp 321–324
Moutiez M, Lippens G, Sergheraert C, Tartar A (1997) Vasopressin trisulphide: synthesis, NMR study and affinity studies with V1 and V2 subtypes receptors. Bioorg Med Chem Lett 7:719–724. https://doi.org/10.1016/S0960-894X(97)00050-4
Mullen DG, Weigel B, Barany G, Distefano MD (2010) On-resin conversion of Cys(Acm)-containing peptides to their corresponding Cys(Scm) congeners. J Pept Sci 16:219–222. https://doi.org/10.1002/psc.1223
Article CAS PubMed Google Scholar
Nielsen RW, Tachibana C, Hansen NE, Winther JR (2011) Trisulfides in proteins. Antiox Redox Signal 15:67–75. https://doi.org/10.1089/ars.2010.3677
Owen MD, Cassidy AL, Weeks AD (2021) Why are women still dying from obstetric hemorrhage? A narrative review of perspectives from high and low resource settings. Int J Obstetric Anesthesia 46:102982. https://doi.org/10.1016/j.ijoa.2021.102982
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