(S)-2,3-dihydroxypropanoic acid hemicalcium salt | 14028-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,3-dihydroxypropanoic acid hemicalcium salt
• 英文别名: L-glyceric acid hemicalcium salt；calcium L-glycerate dihydrate；(S)-glycerate de calcium；L-glyceric acid calcium salt；Calcium-L-glycerat；(S)-2,3-dihydroxy-propionic acid ; calcium salt；(S)-2,3-Dihydroxy-propionsaeure; Calcium-Salz；D-glyceric acid hemicalcium salt
• CAS: 14028-63-8
• 化学式: C₃H₅O₄*0Ca
• 分子量: 125.109
• InChiKey: AWJNHTPICURSMP-DKWTVANSSA-M

物化性质

• 熔点：
  134 °C (dec.)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.29
• 重原子数：
  8.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.59
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2,3-dihydroxypropanoic acid hemicalcium salt 、 蔗糖 在 wild-type sucrose phosphorylase from Leuconostoc mesenteroides produced in E_. coli DH₁₀B cells 作用下， 反应 72.0h， 以33%的产率得到(S)-2-O-α-D-glucopyranosyl glycerate
  参考文献：
  名称：

  Single-step enzymatic synthesis of (R)-2-O-α-d-glucopyranosyl glycerate, a compatible solute from micro-organisms that functions as a protein stabiliser

  摘要：

  在蔗糖作为供体底物存在的情况下，由蔗糖磷酸化酶催化的 R-甘油酯的区域选择性葡萄糖基化提供了天然相容的溶质 (R)-2-O-α-D-吡喃葡萄糖基甘油酯，具有完全区域选择性，优化合成产率为 90% R-甘油已转化且浓度约为 270 mM。

  DOI：

  10.1039/b912621j
• 作为产物：
  描述：

  4-Brom-phenacyl-L-glycerat 在 calcium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (S)-2,3-dihydroxypropanoic acid hemicalcium salt
  参考文献：
  名称：

  苯酚的氧化和生物合成。第十二部分。与吗啡生物碱生物合成有关的立体化学研究

  摘要：

  tri化的salutaridinols-I和-II的臭氧分解反应提供了甘油酸，其绝对构型已通过同位素稀释法确定。这样，吗啡生物碱的前体salutaridinol-I的立体化学已被明确定义。

  DOI：

  10.1039/j39670000128

文献信息

• Synthèse des (<i>R</i>)- et (<i>S</i>)-<i>O</i>-isopropylidène-1,2-glycérols. Détermination de la pureté optique
  作者：Georges Hirth、Willy Walther

  DOI：10.1002/hlca.19850680708

  日期：1985.11.13

  Synthesis of the (R)- and (S)-Glycerol Acetonides. Determination of the Optical Purity

  （R）-和（S）-甘油丙酮酸酯的合成。光学纯度的测定
• Complexation of Lanthanide(III) Ions with Polyhydroxy Carboxylic Acids in Aqueous Solutions
  作者：Sébastien Giroux、Sabrina Aury、Bernard Henry、Patrice Rubini

  DOI：10.1002/1099-0682(200205)2002:5<1162::aid-ejic1162>3.0.co;2-o

  日期：2002.5

  The complexation of lanthanum(III), europium(III), dysprosium(III), erbium(III), and lutetium(III) with D-gluconic acid (LH) was studied by pH potentiometry and NMR. The set of complexes formed in aqueous solutions and their stability constants β were determined, and the results were compared to those previously found for praseodymium(III) (S. Giroux et al., Polyhedron 2000, 19, 1567). A regular evolution

  镧 (III)、铕 (III)、镝 (III)、铒 (III) 和镥 (III) 与 D-葡萄糖酸 (LH) 的络合通过 pH 电位和核磁共振进行了研究。确定了在水溶液中形成的复合物组及其稳定性常数 β，并将结果与​​先前发现的镨 (III) 的结果进行比较（S. Giroux 等人，Polyhedron 2000, 19, 1567）。沿着镧系元素观察到 β 值有规律的演变，特别是对于中性复合物 MLH-2（其中两个羟基官能团被去质子化），其选择性类似于 EDTA。对于 ML2+ 复合物，其中配体通过羧酸根基团配位，13C NMR假接触位移分析表明，羧酸根不是双齿的，α-羟基参与配位。PrIII 与其他羟基羧酸（甘油、苏氨酸、2-羟基丁酸和 3-羟基丁酸）络合的研究证实，在络合物 MLH-2 中，去质子化的羟基与金属离子发生配位α 和 γ 位置相对于羧基的那些。(© Wiley-VCH Verlag
• Structure−Activity Relationships:  Analogues of the Dicaffeoylquinic and Dicaffeoyltartaric Acids as Potent Inhibitors of Human Immunodeficiency Virus Type 1 Integrase and Replication
  作者：Peter J. King、Guoxiang Ma、Wenfang Miao、Qi Jia、Brenda R. McDougall、Manfred G. Reinecke、Chris Cornell、Jean Kuan、Tracey R. Kim、W. Edward Robinson

  DOI：10.1021/jm9804735

  日期：1999.2.1

  The dicaffeoylquinic acids (DCQAs) and dicaffeoyltartaric acids (DCTAs) are potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) integrase. They also inhibit HIV-1 replication at nontoxic concentrations; Since integrase is an excellent target for anti-HIV therapy, structure-activity relationships were employed to synthesize compounds with: (1) improved potency against HIV-1 integrase, (2) improved anti-HIV effect in tissue culture, and (3) increased selectivity as indicated by low cellular toxicity. Thirty-four analogues of the DCTAs and DCQAs were synthesized and tested for cell toxicity, anti-HIV activity, and inhibition of HIV-1 integrase. Seventeen of the 34 analogues had potent activity against HIV-1 integrase ranging from 0.07 to >10 mu M. Seventeen analogues that were synthesized or purchased had no inhibitory activity against integrase at concentrations of 25 mu M. Of the biologically active analogues, 7 of the 17 inhibited HIV replication at nontoxic concentrations. The most potent compounds were D-chicoric acid, meso-chicoric acid, bis(3,4-dihydroxydihydrocinnamoyl)-L-tartaric acid, digalloyl-L-tartaric acid, bis(3,4-dihydroxybenzoyl)-L-tartaric acid, dicaffeoylglyceric acid, and bis(3,4-dihydroxyphenylacetyl)-L-tartaric acid. Anti-HIV activity of the active compounds in tissue culture ranged from 35 to 0.66 mu M. Structure-activity relationships demonstrated that biscatechol moieties were absolutely required for inhibition of integrase, while at least one free carboxyl group was required for anti-HIV activity. These data demonstrate that analogues of the DCTAs and the DCQAs can be synthesized which have improved activity against HIV integrase.
• Syntheses of the l-manno and some other analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1
  作者：Emmanuel Poirot、Xiaodong Zhang、Noel F. Whittaker、Pavol Kováč

  DOI：10.1016/s0008-6215(00)00265-2

  日期：2001.1

  Analogs of the methyl alpha -glycosides of the terminal residues of the O-specific polysaccharides (O-PS) of Vibrio cholerae O:1, serotype Inaba and Ogawa, have been prepared as probes to study their interaction with anti V. cholerae O:1 antibodies. They differ from the termini of the respective O-PSs in anomeric or absolute configuration of perosamine, position of the O-methyl group in D-perosamine, and nature of the N-acyl side chain. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Phenol oxidation and biosynthesis. Part XII. Stereochemical studies related to the biosynthesis of the morphine alkaloids
  作者：D. H. R. Barton、D. S. Bhakuni、R. James、G. W. Kirby

  DOI：10.1039/j39670000128

  日期：——

  and -II has afforded glyceric acids whose absolute configurations have been determined by the isotope dilution method. In this way the stereochemistry of salutaridinol-I, the precursor of the morphine alkaloids, has been defined unambiguously.

  tri化的salutaridinols-I和-II的臭氧分解反应提供了甘油酸，其绝对构型已通过同位素稀释法确定。这样，吗啡生物碱的前体salutaridinol-I的立体化学已被明确定义。