tert-butyl (2S,3S)-2,3-diaminobutanoate | 649554-03-0

• 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
• 英文名称: tert-butyl (2S,3S)-2,3-diaminobutanoate
• CAS: 649554-03-0
• 化学式: C₈H₁₈N₂O₂
• 分子量: 174.243
• InChiKey: OQMNCBISNKYWRQ-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-2,3-diaminobutanoate 在 三氟乙酸 作用下， 以45 mg的产率得到(2S,3S)-2,3-Diamino-butyric acid
  参考文献：
  名称：

  抗-（2S，3S）-和顺-（2R，3S）-二氨基丁酸的不对称合成。

  摘要：

  将同手性N-苄基-N-α-甲基苄基氨基锂加到（E）-肉桂酸叔丁酯或（E）-巴豆酸叔丁酯中，并用叠氮化三苯胺原位胺化，仅形成相应的2-重氮大于95％de的-3-氨基酯 叔丁基（3S，alphaR）-3-N-苄基-N-α-甲基苄基氨基-3-苯基丙酸酯或叔丁基（3S，alphaS）-3-N-苄基-的（E）-烯醇锂的胺化N-α-甲基苄氨基氨基丁酸酯与三叠氮化物以良好的收率和85％的de和> 95％的de生成（2R，3R，alphaR）-和（2S，3S，alphaS）-抗-2-叠氮基-3-氨基酯分别。或者，可以将叔丁基抗-（2S，3S，αS）-2-羟基-3-N-苄基-N-α-甲基苄基氨基丁酸酯选择性地转化为叔丁基抗-（2S，3S，αS）-2-叠氮基-3-N-苄基-N-α-甲基苄基氨基丁酸通过叠氮鎓离子的形成和与叠氮化物的区域选择性打开。（2S，3S，alphaS）-2-叠氮基-3-氨基丁酸叔丁酯通过

  DOI：

  10.1039/b306936m
• 作为产物：
  描述：

  tert-butyl (3S,αS)-3-(N-benzyl-N-α-methylbenzylamino)butanoate 在 叠氮磷酸二苯酯 、 10% Pd(OH)2 on carbon 、 氢气 、 (1S)-(+)-10-樟脑磺哑嗪 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 为溶剂， -78.0~55.0 ℃ 、482.64 kPa 条件下， 反应 103.5h， 生成 tert-butyl (2S,3S)-2,3-diaminobutanoate
  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

• Nine Enzymes Are Required for Assembly of the Pacidamycin Group of Peptidyl Nucleoside Antibiotics
  作者：Wenjun Zhang、Ioanna Ntai、Megan L. Bolla、Steven J. Malcolmson、Daniel Kahne、Neil L. Kelleher、Christopher T. Walsh

  DOI：10.1021/ja2011109

  日期：2011.4.13

  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.
• Asymmetric synthesis of anti-(2S,3S)- and syn-(2R,3S)-diaminobutanoic acidThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
  作者：Mark E. Bunnage、Anthony J. Burke、Stephen G. Davies、Nicholas L. Millican、Rebecca L. Nicholson、Paul M. Roberts、Andrew D. Smith

  DOI：10.1039/b306936m

  日期：——

  azide. Deprotection of tert-butyl (2S,3S,alphaS)-2-azido-3-aminobutanoate via Staudinger reduction, hydrogenolysis and ester hydrolysis furnishes anti-(2S,3S)-diaminobutanoic acid in 98%, de and 98% ee. The asymmetric synthesis of the diastereomeric syn-(2R,3S)-diaminobutanoic acid (98% de and 98% ee) was accomplished via functional group manipulation of tert-butyl anti-(2S,3S,alphaS)-2-hydroxy-3-N-be

  将同手性N-苄基-N-α-甲基苄基氨基锂加到（E）-肉桂酸叔丁酯或（E）-巴豆酸叔丁酯中，并用叠氮化三苯胺原位胺化，仅形成相应的2-重氮大于95％de的-3-氨基酯 叔丁基（3S，alphaR）-3-N-苄基-N-α-甲基苄基氨基-3-苯基丙酸酯或叔丁基（3S，alphaS）-3-N-苄基-的（E）-烯醇锂的胺化N-α-甲基苄氨基氨基丁酸酯与三叠氮化物以良好的收率和85％的de和> 95％的de生成（2R，3R，alphaR）-和（2S，3S，alphaS）-抗-2-叠氮基-3-氨基酯分别。或者，可以将叔丁基抗-（2S，3S，αS）-2-羟基-3-N-苄基-N-α-甲基苄基氨基丁酸酯选择性地转化为叔丁基抗-（2S，3S，αS）-2-叠氮基-3-N-苄基-N-α-甲基苄基氨基丁酸通过叠氮鎓离子的形成和与叠氮化物的区域选择性打开。（2S，3S，alphaS）-2-叠氮基-3-氨基丁酸叔丁酯通过