-N²-isobutyrylpterin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: -N²-isobutyrylpterin
• 英文别名: 2-methyl-N-(4-oxo-3,4-dihydro-2-pteridinyl)propanamide；2-methyl-N-(4-oxo-3H-pteridin-2-yl)propanamide
• 化学式: C₁₀H₁₁N₅O₂
• 分子量: 233.23
• InChiKey: DZMAEFPKWRJQHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  -N²-isobutyrylpterin 在 platinum(IV) oxide 4-二甲氨基吡啶 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 48.0h， 生成 N-{5-[3-(4-benzoylphenyl)-1-oxopropyl]-3,4,5,6,7,8-hexahydro-4-oxopteridin-2-yl}-2-methylpropanamide
  参考文献：
  名称：

  摘要：

  Various 6-substituted pteridines and 5,6,7,8-tetrahydropterins carrying photolabile functions at the side chain (see 7, 20-22, 34-36, 38, and 39) as well as at the 5-position (see 27-29) were synthesized from pterin and from 6-phenylpterin (1) and 6-(hydroxymethyl)pterin (10). Attachment of the photoaffinity labels via ester bonds required a special protecting-group strategy based upon acid-labile (see 30-33) and beta -eliminating blocking groups (see 17-19). The 6-(4-azidophenyl)pterin (7) was obtained from 6-phenylpterin (1) via intermediates 2 and 4-6, due to the low solubility of simple pterins in general. The pteridine derivatives 21 22, 25, 26, 28, 29, 32, 33, 35, 36, 38, and 39 were screened as inhibitors of neuronal (type I) NO synthase (see Table) from porcine cerebellum, of which 22, 35, 36, and 38 showed interesting inhibitory activity with similar potency and effectiveness.

  DOI：

  10.1002/1522-2675(20001004)83:10<2738::aid-hlca2738>3.0.co;2-a
• 作为产物：
  描述：

  2-氨基-4-羟基蝶啶 、 异丁酸酐 在 吡啶 作用下， 反应 5.0h， 以76.9%的产率得到-N²-isobutyrylpterin
  参考文献：
  名称：

  链接非核糖体肽和蝶啶生物合成机制在光致发光中的缩合域的功能表征。

  摘要：

  非核糖体肽合成酶（NRPS）产生各种生物学上重要的小分子。NRPS可以与其他酶相互作用形成混合生物合成系统，从而扩展其产品的结构和功能多样性。肽苷是光致发光菌中前所未有的蝶啶-NRPS型杂化生物合成基因簇编码的代谢物，但尚未在生化水平上检验独特的酶系统如何相互作用以产生这些分子。通过未知的机制，遗传位点还可以影响涉及自动诱导剂和次级代谢产物生物合成的其他酶的调控。在这里，通过体外蛋白质生化分析，我们证明了该途径中存在的非典型NRPS缩合（C）结构域将衍生自α-酮酸的酰基单元缩合到自由的5,6,7,8-四氢蝶呤核心上，从而产生叔顺式-含酰胺的肽核苷。化学合成分子的溶液研究导致了与天然产物中观察到的相同的酰胺区域化学反应。由C结构域介导的生化转化破坏了其氧化还原活性四氢蝶呤底物的自由基清除活性。二级代谢产物分析表明，肽吡啶基因座会影响与群体感应，抗菌和共生相关的某些代谢途径。两者合计，结果表明

  DOI：

  10.1021/acs.biochem.7b00863

文献信息

• Pteridines, Part CXIII
  作者：Qizheng Yao、Wolfgang Pfleiderer

  DOI：10.1002/hlca.200390025

  日期：2003.1

  compounds can be alkylated under Mitsunobu conditions to form from N2-acylpterins (see 2 and 3) and their derivatives (see 5, 6, 8, 9, 11, 13, 15, and 17) selectively the O4-alkyl derivatives 22–31, whereas the electron-donating [(dimethylamino)methyleneamino function in 46–51 gives, in a selective reaction, the N(3)-substitution (52–61). N2,N2-Dimethylpterins and 18 and 19 and N2-methylpterins 20 and 21

  蝶呤的低溶解度可通过N 2-酰化或形成N 2 -[（（二甲基氨基）亚甲基]衍生物而大大改善。这两种类型的化合物可以下被烷基化的Mitsunobu条件从到形式Ñ 2 -acylpterins（参照2和3）和它们的衍生物（参见图5，6，8，9，11，13，15，和17）选择性地将Ò 4 -烷基衍生物22 – 31，而给电子体[[（二甲基氨基）亚甲基氨基]在46 – 51在选择性反应中给出N（3）取代（52 – 61）。Ñ 2，Ñ 2个-Dimethylpterins和18个19和Ñ 2 -methylpterins 20和21直接烷基化还向Ò 4位上（32 - 35，38和39）。脱酰可以在非常温和的条件下通过溶剂解用MeOH（实现22 40，26 41），和所述的位移Ò 4- [2-（4-硝基苯基）乙基]基团在室温下，以相应的蝶啶-2,4-二胺氨前进42 - 45。N 2 -[（（二甲基氨基）亚甲基]基团的裂解可很好地与氨（62
• Pteridines CXX. Synthesis and Properties of Tetrahydropterins Coupled to 1,4-Dihydropyridines
  作者：Wolfgang Pfleiderer、Joachim Rehse

  DOI：10.3987/com-08-s(f)70

  日期：——

  N(2)-Isobutyroyl-5,6,7,8-tetrahydropterins (6-10) have been coupled with nicotinic acid to form the N(5)-nicotinoyl derivatives 11-15. Quaternization at the pyridine moiety led to 19-31 which can be reduced to the corresponding N-substituted 1,4-dihydropyridine dertivatives 35-39. Partial deacylation of the isobutyroyl group afforded the various types of terahydropterins 16-18, 32-34 and 40-42. The newly synthesized 5,6,7,8-tetrahydropterin derivatives have been characterized by pK(a)-determinations, UV- and NMR-spectra as well as elemental analyses.
• Functional Characterization of a Condensation Domain That Links Nonribosomal Peptide and Pteridine Biosynthetic Machineries in <i>Photorhabdus luminescens</i>
  作者：Corey E. Perez、Hyun Bong Park、Jason M. Crawford

  DOI：10.1021/acs.biochem.7b00863

  日期：2018.1.23

  producing the tertiary cis-amide-containing pepteridines. Solution studies of the chemically synthesized molecules led to the same amide regiochemistries that were observed in the natural products. The biochemical transformations mediated by the C domain destroy the radical scavenging activity of its redox active tetrahydropterin substrate. Secondary metabolite analyses revealed that the pepteridine locus

  非核糖体肽合成酶（NRPS）产生各种生物学上重要的小分子。NRPS可以与其他酶相互作用形成混合生物合成系统，从而扩展其产品的结构和功能多样性。肽苷是光致发光菌中前所未有的蝶啶-NRPS型杂化生物合成基因簇编码的代谢物，但尚未在生化水平上检验独特的酶系统如何相互作用以产生这些分子。通过未知的机制，遗传位点还可以影响涉及自动诱导剂和次级代谢产物生物合成的其他酶的调控。在这里，通过体外蛋白质生化分析，我们证明了该途径中存在的非典型NRPS缩合（C）结构域将衍生自α-酮酸的酰基单元缩合到自由的5,6,7,8-四氢蝶呤核心上，从而产生叔顺式-含酰胺的肽核苷。化学合成分子的溶液研究导致了与天然产物中观察到的相同的酰胺区域化学反应。由C结构域介导的生化转化破坏了其氧化还原活性四氢蝶呤底物的自由基清除活性。二级代谢产物分析表明，肽吡啶基因座会影响与群体感应，抗菌和共生相关的某些代谢途径。两者合计，结果表明
• ——
  作者：Viola Groehn、Lothar Fröhlich、Harald H. H. W. Schmidt、Wolfgang Pfleiderer

  DOI：10.1002/1522-2675(20001004)83:10<2738::aid-hlca2738>3.0.co;2-a

  日期：2000.10.4

  Various 6-substituted pteridines and 5,6,7,8-tetrahydropterins carrying photolabile functions at the side chain (see 7, 20-22, 34-36, 38, and 39) as well as at the 5-position (see 27-29) were synthesized from pterin and from 6-phenylpterin (1) and 6-(hydroxymethyl)pterin (10). Attachment of the photoaffinity labels via ester bonds required a special protecting-group strategy based upon acid-labile (see 30-33) and beta -eliminating blocking groups (see 17-19). The 6-(4-azidophenyl)pterin (7) was obtained from 6-phenylpterin (1) via intermediates 2 and 4-6, due to the low solubility of simple pterins in general. The pteridine derivatives 21 22, 25, 26, 28, 29, 32, 33, 35, 36, 38, and 39 were screened as inhibitors of neuronal (type I) NO synthase (see Table) from porcine cerebellum, of which 22, 35, 36, and 38 showed interesting inhibitory activity with similar potency and effectiveness.