Isolation, identification, and synthesis of a disulfated sulfakinin from the central nervous system of an arthropods the white shrimp Litopenaeus vannamei

Toward a framework for sulfoproteomics: Synthesis and characterization of sulfotyrosine‐containing peptides

“…86 Most commonly, Tyr sulfation is achieved by treatment with concentrated sulfuric acid in the cold [43][44][45][87][88][89] or with a complex of sulfur trioxide with either pyridine 38,80,84,[89][90][91][92] or DMF. 75,93,94 With concentrated sulfuric acid, control of reaction temperature and time are crucial to achieve quantitative sulfation and minimize sulfonation as a side reaction.…”

“…87 The undesired sulfation of these residues can sometimes be avoided by a segment synthesis strategy 89 ; however, the use of orthogonally removable protecting groups provides a more general approach to solving this problem. 44,45,75,90,93,94 For example, to achieve selective sulfation of specific Tyr residues in peptides synthesized by Fmocbased solid-phase chemistry, Futaki et al introduced the p-(methylsulphinyl)benzyl (Msib) group to protect the sidechains of Ser, Thr, and Tyr and the Msz group to protect the N-a-amino and e-amino groups. 75,94 The TFA-stable Msib and Msz groups are not removed during cleavage and deprotection of the peptide-resin.…”

“…37 Tyr sulfation is not limited to proteins but also occurs in bioactive peptides isolated from a wide range of vertebrate and invertebrate organisms (Table I). These include peptide hormones and neuropeptides of the gastrin/cholecystokinin (CCK) family, 17,[38][39][40][41][42][43][44][45][46][47][48] Leu-enkephalin, 49 and bradykinin-related peptides, referred to as phyllokinins, from the skin of the South American frog Phyllomedusa rohdei. 50 Tyr sulfation also occurs in certain a-conotoxins that have been isolated from the venoms of various cone snail species and act as potent antagonists of neuronal nicotinic acetylcholine receptors.…”

“…While there are currently no sulfoTyr specific metal affinity methods, there have been two recent studies reporting the development of sequence-independent monoclonal anti-sulfoTyr antibodies which could be useful for the enrichment and detection of sulfoTyr-containing peptides. 147,148 Although sulfation sites could be assigned infrequently by low-energy CID-MS/MS due to partial retention of the sulfoester group in the observed fragment ions, 45,148 in most cases only the sequence of the unsulfated peptide without information on the sulfation sites could be obtained. However, retention of the sulfoester group in backbone cleavage fragment ions is more commonly observed in negative ion mode high-energy CID-MS/MS experiments.…”

From genes to behavior: investigations of neurochemical signaling come of age for the model crustacean Daphnia pulex

“…Given its minute size and the need to manually dissect a sufficient amount of starting material, the identification of even a single Daphnia neuropeptide via this strategy would surely have been daunting, as hundreds, and in some cases thousands, of central nervous systems (CNSs) were needed for the biochemical isolation and characterization of individual native peptides from much larger crustaceans (e.g. Torfs et al, 2002). Similarly, the de novo sequencing of peptide precursor protein and receptor genes/transcripts, as well as those encoding the biosynthetic enzymes, transporters and receptors involved in amine, diffusible gas and small molecule transmitter neurotransmission, is time consuming on an individual level, and to achieve full, or at least near complete, coverage for all signaling systems, would at best have been an expensive, labor-intensive, multi-year undertaking.…”