D-alanyl-D-serine | 1115-50-0

• 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: D-alanyl-D-serine
• 英文别名: (2R)-2-[[(2R)-2-aminopropanoyl]amino]-3-hydroxypropanoic acid
• CAS: 1115-50-0
• 化学式: C₆H₁₂N₂O₄
• 分子量: 176.17
• InChiKey: IPWKGIFRRBGCJO-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  adenosine 5'-triphosphate 、 D-丙氨酸 、 D-丝氨酸 生成 adenosine 5'-diphosphate 、 D-alanyl-D-serine 、 氢(+1)阳离子 、 H3PO4
  参考文献：
  名称：

  Bacterial resistance to vancomycin: Overproduction, purification, and characterization of VanC2 from Enterococcus casseliflavus as a d -Ala- d -Ser ligase

  摘要：

  VanC表型是肠球菌对万古霉素的临床耐药性，表现为Enterococcus gallinarum和Enterococcus casseliflavus。基于检测到的细胞前体UDP-N-乙酰葡萄糖胺肽五肽中止于d-Ala-d-Ser而不是d-Ala-d-Ala，预测VanC连接酶将是d-Ala-d-Ser而不是d-Ala-d-Ala连接酶。在Escherichia coli中过度表达E. casseliflavus ATCC 25788 vanC2基因并纯化至同质性，证明了ATP依赖性d-Ala-d-Ser连接酶活性。d-Ala-d-Ser/d-Ala-d-Ala二肽形成的kcat/Km2（Km2 = d-Ser或C-末端d-Ala的Km）比率为270/0.69，对C-末端位置的d-Ala选择性高达400倍。VanC2还具有相当大的d-Ala-d-Asn连接酶活性（kcat/Km2 = 74 mM-1·min-1）。

  DOI：

  10.1073/pnas.94.19.10040

文献信息

• Derivatives of glycinergic r(+)-2-amino-3-hydroxypropanoic acid
  申请人：Clarence-Smith Kathleen

  公开号：US20050261372A1

  公开（公告）日：2005-11-24

  The use of R(+)-2-amino-3-hydroxypropanoic acid derivatives, nitrogen substituted by a (C 1 -C 6 )alkyl, (C 3 -C 6 )alkenyl, 3-oxo(C 5 -C 6 )alkyl, 3-oxo(C 4 -C 6 )alken-2-yl, phenyl(C 1 -C 6 )alkyl, phenyl(C 2 -C 6 )alkenyl, gem-diphenyl(C 1 -C 6 )alkyl, gem-diphenyl(C 2 -C 6 )alkenyl, (C 1 -C 6 )alcanoyl, optionally N-substituted alanyl, optionally N,N′-disubstituted lysinoyl, phenyl(C 1 -C 6 )alkylydene or gem-diphenyl(C 1 -C 6 )alkylidene group, and of the pharmaceutically acceptable salts thereof, for preparation of medicaments intended for the treatment of CNS diseases due to reduced glycinergic transmission, particularly for the treatment of autism, schizophrenia and Alzheimer's disease, is described.

  描述了使用R(+)-2-氨基-3-羟基丙酸衍生物的用途，氮被(C1-C6)烷基，(C3-C6)烯基，3-氧代(C5-C6)烷基，3-氧代(C4-C6)烯基，苯基(C1-C6)烷基，苯基(C2-C6)烯基，双苯基(C1-C6)烷基，双苯基(C2-C6)烯基，(C1-C6)醇酰基，可选择地N-取代丙氨酰基，可选择地N,N′-二取代赖氨酰基，苯基(C1-C6)烷基亚烯基或双苯基(C1-C6)烷基亚烯基团及其药学上可接受的盐，用于制备用于治疗由于甘氨酸递质传递减少而引起的中枢神经系统疾病的药物，特别是用于治疗自闭症、精神分裂症和阿尔茨海默病。
• Sequence of the vanC gene of Enterococcus gallinarum BM4174 encoding a d-alanine:d-alanine ligase-related protein necessary for vancomycin resistance
  作者：Sylvie Dutka-Malen、Catherine Molinas、Michel Arthur、Patrice Courvalin

  DOI：10.1016/0378-1119(92)90302-6

  日期：1992.3

  The amplification product obtained with DNA from vancomycin-resistant (Vm(R)) Enterococcus gallinarum BM4174 and a pair of degenerate oligodeoxyribonucleotides that correspond to conserved amino acid (aa) motifs in Escherichia coli D-alanine (D-Ala):D-Ala ligases and in En. faecium Vm(R) protein (VanA) was used as a probe to clone the vanC gene of that strain. The vanC product, with a calculated M(r) of 37504, exhibits 29 to 38% aa identity with VanA and E. coli ligases. Insertional inactivation of vanC led to Vm sensitivity of BM4174 suggesting that the gene may encode a D-Ala:D-Ala ligase of altered specificity.
• US7488755B2
  申请人：——

  公开号：US7488755B2

  公开（公告）日：2009-02-10
• Bacterial resistance to vancomycin: Overproduction, purification, and characterization of VanC2 from <i>Enterococcus casseliflavus</i> as a <scp>d</scp> -Ala- <scp>d</scp> -Ser ligase
  作者：Il-Seon Park、Chun-Hung Lin、Christopher T. Walsh

  DOI：10.1073/pnas.94.19.10040

  日期：1997.9.16

  The VanC phenotype for clinical resistance of enterococci to vancomycin is exhibited by Enterococcus gallinarum and Enterococcus casseliflavus . Based on the detection of the cell precursor UDP- N -acetylmuramic acid pentapeptide intermediate terminating in d -Ala- d -Ser instead of d -Ala- d -Ala, it has been predicted that the VanC ligase would be a d -Ala- d -Ser rather than a d -Ala- d -Ala ligase. Overproduction of the E. casseliflavus ATCC 25788 vanC2 gene in Escherichia coli and its purification to homogeneity allowed demonstration of ATP-dependent d -Ala- d -Ser ligase activity. The k _cat / K _m2 ( K _m2 = K _m for d -Ser or C-terminal d -Ala) ratio for d -Ala- d -Ser/ d -Ala- d -Ala dipeptide formation is 270/0.69 for a 400-fold selection against d -Ala in the C-terminal position. VanC2 also has substantial d -Ala- d -Asn ligase activity ( k _cat / K _m2 = 74 mM ⁻¹ min ⁻¹ ).

  VanC表型是肠球菌对万古霉素的临床耐药性，表现为Enterococcus gallinarum和Enterococcus casseliflavus。基于检测到的细胞前体UDP-N-乙酰葡萄糖胺肽五肽中止于d-Ala-d-Ser而不是d-Ala-d-Ala，预测VanC连接酶将是d-Ala-d-Ser而不是d-Ala-d-Ala连接酶。在Escherichia coli中过度表达E. casseliflavus ATCC 25788 vanC2基因并纯化至同质性，证明了ATP依赖性d-Ala-d-Ser连接酶活性。d-Ala-d-Ser/d-Ala-d-Ala二肽形成的kcat/Km2（Km2 = d-Ser或C-末端d-Ala的Km）比率为270/0.69，对C-末端位置的d-Ala选择性高达400倍。VanC2还具有相当大的d-Ala-d-Asn连接酶活性（kcat/Km2 = 74 mM-1·min-1）。