Fujii N, Hayashi Y, Katakura S, Akaji K, Yajima H, Inouye A, Segawa T
Int J Pept Protein Res. 1985 Aug;26(2):121-9.
A decapeptide corresponding to the entire amino acid sequence of neurokinin A, a porcine spinal cord peptide, was synthesized in a conventional manner using protecting groups removable by 1 M TFMSA-thioanisole in TFA. The HS-CH2CH2CO group was introduced onto the synthetic neurokinin A by reaction of 3-(S-acetyl-thiopropionyl)-thiazolidine-2-thione, followed by deacetylation with hydroxylamine. 2,4-Dinitrophenyl-p-(beta-nitrovinyl)-benzoate trapped the above HS-CH2CH2CO-neurokinin A derivative in acidic media, then BSA in basic media in nearly quantitative yield. A similar decapeptide, neurokinin B, was also synthesized and conjugated onto BSA using an alternative SH-introducing reagent, 3-(S-p-methoxybenzyl-thiopropionyl)-thiazolidine-2-thione, and the above heterobifunctional conjugating reagent.
以常规方式合成了一种与神经激肽A（一种猪脊髓肽）的完整氨基酸序列相对应的十肽，该合成过程使用了可在三氟乙酸中被1 M三氟甲磺酸苯甲硫醚除去的保护基团。通过3-(S-乙酰基-硫代丙酰基)-噻唑烷-2-硫酮反应，随后用羟胺进行脱乙酰化反应，将HS-CH2CH2CO基团引入到合成的神经激肽A上。2,4-二硝基苯基-p-(β-硝基乙烯基)-苯甲酸酯在酸性介质中捕获上述HS-CH2CH2CO-神经激肽A衍生物，然后在碱性介质中与牛血清白蛋白（BSA）反应，产率几乎为定量。使用另一种引入巯基的试剂3-(S-对甲氧基苄基-硫代丙酰基)-噻唑烷-2-硫酮和上述异双功能偶联试剂，也合成了类似的十肽神经激肽B，并将其偶联到BSA上。
