3-氨基磺酰基丙氨酸 | 18625-03-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3-氨基磺酰基丙氨酸
• 英文名称: (L)-3-aminosulfonylalanine
• 英文别名: Cys(SO₂NH₂)；3-Sulfamoyl-L-alanin；L-2-Amino-2-carboxyethansulfonamid；L-2-Amino-3-sulfamoylpropionsaeure；(R)-2-amino-3-sulfamoyl-propionic acid；(R)-2-Amino-3-sulfamoyl-propionsaeure；β-sulfamoylalanine；3-sulfamoyl-L-alanine；L-3-sulfamoyl-alanine；(2R)-2-amino-3-sulfamoylpropanoic acid
• CAS: 18625-03-1
• 化学式: C₃H₈N₂O₄S
• 分子量: 168.174
• InChiKey: WDOCIKSRUBWQFT-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-2-benzyloxycarbonylamino-3-sulfamoylpropanoic acid ethyl ester 生成 3-氨基磺酰基丙氨酸
  参考文献：
  名称：

  Aleksiev; Stoev, Pharmazie, 1971, vol. 26, # 8, p. 469 - 473

  摘要：

  DOI：

文献信息

• 3-氨基磺酰基丙氨酸的制备方法
  申请人：西北工业大学

  公开号：CN112142629B

  公开（公告）日：2021-09-14

  本发明涉及化合物制备领域，具体地，涉及式(I)所示3‑磺胺基‑丙氨酸的制备方法。本发明以市售L/D‑胱氨酸双(叔丁酯)二盐酸盐为原料，经Boc保护，氧化反应，脱保护3步反应可高效的制备得到式(I)所示化合物，与已报道的路线相比，避开了使用氯气和氨气刺激性毒性气体，合成路线短，且收率高，后处理方法简便,具有很好的工业价值。
• Potential inhibitors of L-asparagine biosynthesis. 4. Substituted sulfonamide and sulfonylhydrazide analogs of L-asparagine
  作者：Steven Brynes、Gilbert J. Burckart、Michael Mokotoff

  DOI：10.1021/jm00199a008

  日期：1978.1

  Several N-substituted sulfonamides and N'-substituted sulfonylhydrazides have been prepared as sulfur analogues of L-asparagine with the potential of acting as inhibitors of L-asparagine synthetase (ASase, from Novikoff hepatoma). L-Cysteine was converted in known steps to N-carboxy-3-(sulfonylchloro)-L-alanine dibenzyl ester (1). Condensation of 1 with O-benzylhydroxylamine, p-(fluorosulfonyl)benzylamine, or monoethyl fumarylhydrazide (9), followed by deblocking with HF, gave 3-(hydroxysulfamoyl)-L-alanine (3a), 3-[p-(fluorosulfonylbenzyl)]sulfamoyl-L-alanine (3c), and 3-sulfo-L-alanine S-[2-[(E)-3-(ethoxycarbonyl)acryloyl]hydrazide] (3e), respectively. Similarly, 1 with 2-chloroethylamine and deblocking with H2-Pd gave 3-[(2-chloroethyl)sulfamoyl]-L-alanine (3b). tert-Butyl carbazate was allowed to react with 1 and the tert-butyl group was removed with HCl. The resulting sulfonylhydrazide 7 was condensed with p-(fluorosulfonyl)benzoyl chloride and then deblocked with HF to give 3-sulfo-L-alanine S-[2-[P-(fluorosulfonyl)benzoyl]hydrazide] (3d). The inhibition of ASase by 3a-e at 2 mM was 97, 0, 30, 43, and 37%, respectively, and 3a was competitive with L-aspartic acid. Neither 3a nor 3e was effective in increasing the life span of mice bearing P-388 lymphocytic leukemia.
• Notes: 2-Amino-2-carboxyethanesulfonamide
  作者：Donald Ross、Charles Skinner、William Shive

  DOI：10.1021/jo01091a627

  日期：1959.9
• The Preparation and Some Biological Properties of the Asparagine Analog L-2-Amino-2-carboxyethanesulfonamide
  作者：Hans Heymann、T. Ginsberg、Z. R. Gulick、E. A. Konopka、R. L. Mayer

  DOI：10.1021/ja01528a026

  日期：1959.10
• Aleksiev; Stoev, Pharmazie, 1971, vol. 26, # 8, p. 469 - 473
  作者：Aleksiev、Stoev

  DOI：——

  日期：——