(2R,8aS)-(+)-(camphorylsulfonyl)oxaziridine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,8aS)-(+)-(camphorylsulfonyl)oxaziridine
• 英文别名: [4aS-(4a,7,8aR)]-tetrahydro-9,9-dimethyl-4H-4A,7-methanooxazirino[3,2-i][2,1]benzisothiazole 3,3-dioxide；(+)-(2R,8aS)-10-camphorylsulfonyloxaziridine；(-)-(10-camphorsulfonyloxaziridine)；(1S,6R,8R)-11,11-dimethyl-5-oxa-3lambda6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide；(1S,6R,8R)-11,11-dimethyl-5-oxa-3λ6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane 3,3-dioxide
• 化学式: C₁₀H₁₅NO₃S
• 分子量: 229.3
• InChiKey: GBBJBUGPGFNISJ-KSNGIRGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,8aS)-(+)-(camphorylsulfonyl)oxaziridine 、 phenylmagnesium bromide 以96%的产率得到
  参考文献：
  名称：

  DAVIS, FRANKLIN A.;WEI, JIA;SHEPPARD, AURELIA C.;GUBERNICK, STEVEN, TETRAHEDRON LETT., 28,(1987) N 43, 5115-5118

  摘要：

  DOI：
• 作为产物：
  描述：

  D(+)-10-樟脑磺酸 在 Oxone 、 ammonium hydroxide 、 氯化亚砜 、 potassium carbonate 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 9.75h， 生成 (2R,8aS)-(+)-(camphorylsulfonyl)oxaziridine
  参考文献：
  名称：

  (+)-(2R,8aS)-10-(CAMPHORYLSULFONYL)OXAZIRIDINE

  摘要：

  DOI：

  10.15227/orgsyn.069.0158
• 作为试剂：
  描述：

  tert-butyl (3R,αR)-3-(N-benzyl-N-α-methylbenzylamino)butanoate 在 (2R,8aS)-(+)-(camphorylsulfonyl)oxaziridine 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 (2R,3R,αR)-tert-butyl 2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)butanoate
  参考文献：
  名称：

  Nine Enzymes Are Required for Assembly of the Pacidamycin Group of Peptidyl Nucleoside Antibiotics

  摘要：

  Pacidamycins are a family of uridyl peptide antibiotics that inhibit the translocase MraY, an essential enzyme in bacterial cell wall biosynthesis that to date has not been clinically targeted. The pacidamycin structural skeleton contains a doubly inverted peptidyl chain with a beta-peptide and a ureido linkage as well as a 3'-deoxyuridine nucleoside attached to DABA(3) of the peptidyl chain via an enamide linkage. Although the biosynthetic gene cluster for pacidamycins was identified recently, the assembly line of this group of peptidyl nucleoside antibiotics remained poorly understood because of the highly dissociated nature of the encoded nonribosomal peptide synthetase (NRPS) domains and modules. This work has identified a minimum set of enzymes needed for generation of the pacidamycin scaffold from amino acid and nucleoside monomers, highlighting a freestanding thiolation (T) domain (PacH) as a key carrier component in the peptidyl chain assembly as well as a freestanding condensation (C) domain (PacI) catalyzing the release of the assembled peptide by a nucleoside moiety. On the basis of the substrate promiscuity of this enzymatic assembly line, several pacidamycin analogues were produced using in vitro total biosynthesis.

  DOI：

  10.1021/ja2011109

文献信息

• DAVIS, FRANKLIN A.;WEI, JIA;SHEPPARD, AURELIA C.;GUBERNICK, STEVEN, TETRAHEDRON LETT., 28,(1987) N 43, 5115-5118
  作者：DAVIS, FRANKLIN A.、WEI, JIA、SHEPPARD, AURELIA C.、GUBERNICK, STEVEN

  DOI：——

  日期：——
• (+)-(2R,8aS)-10-(CAMPHORYLSULFONYL)OXAZIRIDINE
  作者：Towson, James C.、Weismiller, Michael C.、Lal, G. Sankar、Sheppard, Aurelia C.、Kumar, Anil、Davis, Franklin A.

  DOI：10.15227/orgsyn.069.0158

  日期：——