Z(OMe)-Arg(Mts)-OSu | 78452-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z(OMe)-Arg(Mts)-OSu
• CAS: 78452-49-0
• 化学式: C₂₈H₃₅N₅O₉S
• 分子量: 617.68
• InChiKey: PLILYCAVWMBRDO-QFIPXVFZSA-N

反应信息

• 作为反应物：
  描述：

  Z(OMe)-Arg(Mts)-OSu 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以88%的产率得到
  参考文献：
  名称：

  Kubota, Minoru; Nagase, Osamu; Yajima, Haruaki, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 4, p. 1169 - 1171

  摘要：

  DOI：

文献信息

• Studies on peptides. CLX. Synthesis of a 33-residue peptide corresponding to the entire amino acid sequence of human cholecystokinin (hCCK-33).
  作者：NOBUTAKA FUJII、SHIROH FUTAKI、SUSUMU FUNAKOSHI、KENICHI AKAJI、HIROSHI MORIMOTO、RYUICHIRO DOI、KAZUTOMO INOUE、MASAFUMI KOGIRE、SHOICHIRO SUMI、MITSUTOSHI YUN、TAKAYOSHI TOBE、MITSURU AONO、MASAYUKI MATSUDA、HIROAKI NARUSAWA、MOTOYUKI MORIGA、HARUAKI YAJIMA

  DOI：10.1248/cpb.36.3281

  日期：——

  An unsulfated form of human cholecystokinin (hCCK-33) was synthesized by successive azide condensations of seven peptide fragments, followed by deprotection with 1 M trimethylsilyl trifluoromethanesulfonate/trifluoroacetic acid. The phenolic group of Tyr (position 27) was selectively sulfated with pyridine-SO3 complex, after reversible masking of other functional groups with hard base (F-)-labile protecting groups, i.e., the amino functions with 9-fluorenyl-methyloxycarbonyl group and the hydroxyl functions of 4 Ser residues with tert-butyldiphenylsilyl groups. In terms of pancreatic protein output and capillary blood flow in dogs, the relative potency of synthetic hCCK-33 with respect to that of synthetic CCK-8 (taken as 1 on a molar basis) was 0.9. In terms of gastric acid and pepsin output in rat in vivo assays, synthetic hCCK-33 was about 2- to 3-fold more potent than CCK-8 on a molar basis.

  一种人胆囊收缩素（hCCK-33）的非硫酸化形式通过七个肽片段的连续叠氮化缩合合成，随后用1 M三甲基硅烷三氟甲磺酸盐/三氟乙酸去保护。Tyr（位置27）的酚羟基在用具有硬碱性（F-）的保护基团可逆掩蔽其他功能基团后，选择性地与吡啶-SO3复合物进行硫酸化，即用9-氟烯基-甲氧基羧基基团保护氨基功能，以及用叔丁基二苯基硅基团保护4个丝氨酸残基的羟基功能。在犬的胰腺蛋白输出和毛细血管血流方面，合成的hCCK-33相对于合成的CCK-8（以1为摩尔基准）的相对效力为0.9。在大鼠体内实验中，合成的hCCK-33在胃酸和胃蛋白酶的输出方面，其效力比CCK-8高约2到3倍。