[1-13C]-L-isoleucine

• 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: [1-13C]-L-isoleucine
• 英文别名: L-Isoleucine-1-13C；(2S,3S)-2-amino-3-methyl(113C)pentanoic acid
• 化学式: C₆H₁₃NO₂
• 分子量: 132.164
• InChiKey: AGPKZVBTJJNPAG-XDXFPRKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [1-13C]-L-isoleucine 在 4 A molecular sieve 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 26.0h， 生成 [13C₂]-N-benzyloxycarbonyl-L-tryptophanyl-L-isoleucine benzyl ester
  参考文献：
  名称：

  Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework

  摘要：

  It has been previously established in this laboratory that the beta -methyl-beta -hydroxyproline moiety of the potent anthelmintic agent paraherquamide A, is biosynthetically derived from L-isoleucine. The downstream events from L-Ile to paraherquamide A have now been investigated. The synthesis of [1-(13)C]-labeled L-beta -methylproline is described by means of a Hoffman-Loeffler-Freytag reaction sequence from [1-(13)C]-L-Ile. This amino acid is shown to be a direct biosynthetic precursor to paraherquamide A by feeding and incorporation experiments in growing cultures of Penicillum fellutanum. Three tryptophan-containing dipeptides of L-beta -methylproline have been constructed: [(13)C(2)]-2-(l,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline [(13)C(2)]-3(S)-methyl-L-prolyl-2-(l,1-dimethyl-2-propenyl)-L-tryptophan and [(13)C(2)]-cyclo-2-(l,1-dimethyl-2-propenyl)-L-tryptophan-3(S)-methyl-L-proline. [alpha-(15)N, 1-(13)C]-2-(1,1-Dimethyl-2-propenyl)-L-tryptophan was also prepared but none of these substances were found to serve as biosynthetic precursors to paraherquamide A. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00449-5

文献信息

• Phosphonopeptide K-26 biosynthetic intermediates in Astrosporangium hypotensionis
  作者：Ioanna Ntai、Vanessa V. Phelan、Brian O. Bachmann

  DOI：10.1039/b611768f

  日期：——

  Precursors and advanced intermediates for phosphonopeptide K-26 biosynthesis were synthesized and incorporation studies in Astrosporangium hypotensionis suggest a new mechanism of C–P bond formation in aromatic phosphonates.

  合成了膦酰肽 K-26 生物合成的前体和高级中间体，并在 Astrosporangium hypotensionis 中进行了掺入研究，结果表明芳香族膦酸盐中 C-P 键形成的新机制。
• A Simple and Economical Method for the Production of ¹³C,¹⁸O-Labeled Fmoc-Amino Acids with High Levels of Enrichment:  Applications to Isotope-Edited IR Studies of Proteins
  作者：James Marecek、BenBen Song、Scott Brewer、Jenifer Belyea、R. Brian Dyer、Daniel P. Raleigh

  DOI：10.1021/ol701913p

  日期：2007.11.1

  Isotope-edited IR of proteins has generated considerable interest. Double labeling with C-13 and O-18 with high levels of isotopic enrichment is required for residue-specific resolution. Current methods for the preparation of doubly labeled amino acids give modest O-18 enrichment, limiting the utility of the approach. We report a simple and economical method for preparing C-13,O-18-doubly labeled N-(9-fluorenylmethoxycarbonyl)-amino acids with high levels of enrichment for residues that do not require acid-labile side-chain protecting groups.
• PARRY, RONALD J.;LIN, MING-TEH;WALKER, ALAN E.;MHASKAR, SUNIL, J. AMER. CHEM. SOC., 113,(1991) N, C. 1849-1850
  作者：PARRY, RONALD J.、LIN, MING-TEH、WALKER, ALAN E.、MHASKAR, SUNIL

  DOI：——

  日期：——
• IR Study of Cross-Strand Coupling in a β-Hairpin Peptide Using Isotopic Labels
  作者：Vladimír Setnička、Rong Huang、Catherine L. Thomas、Marcus A. Etienne、Jan Kubelka、Robert P. Hammer、Timothy A. Keiderling

  DOI：10.1021/ja043007f

  日期：2005.4.1

  Model beta-hairpin peptides can be used to develop understanding of fundamental elements of beta-sheet secondary structure formation and stability. We have studied two 13C-labeled variants of a beta-hairpin peptide modified from a design originally proposed by Gellman: Arg-Tyr-Val-Glu-Val-Aib-Gly-Lys-Lys-Ile-Leu-Gln. (In this peptide, the two italicized residues form a beta-turn, while 13C-labels are on the amide C=O of Val3, Lys8 in HBG-L and Val3, Ile10 in HBG-S.) Both these peptides are labeled on opposite strands of the hairpin, but differ in the labeling pattern. One (HBG-L) forms a large (14-atom) H-bonded ring of labeled C=Os, while the other (HBG-S) forms a small (10-atom) H-bonded ring. These impact the amide I infrared spectra, with HBG-L having a 13C frequency and intensity higher than that of HBG-S, in good agreement with our spectral simulations based on quantum mechanically derived force fields. The thermal behavior of both peptides yields a broad thermal transition and lacks an isosbestic point. The 13C band for HBG-L has the largest intensity change with temperature, distinct from the 12C change and the HBG-S 13C change.
• Studies on the biosynthesis of paraherquamide. Construction of the amino acid framework
  作者：Emily M Stocking、Juan F Sanz-Cervera、Clifford J Unkefer、Robert M Williams

  DOI：10.1016/s0040-4020(01)00449-5

  日期：2001.6

  It has been previously established in this laboratory that the beta -methyl-beta -hydroxyproline moiety of the potent anthelmintic agent paraherquamide A, is biosynthetically derived from L-isoleucine. The downstream events from L-Ile to paraherquamide A have now been investigated. The synthesis of [1-(13)C]-labeled L-beta -methylproline is described by means of a Hoffman-Loeffler-Freytag reaction sequence from [1-(13)C]-L-Ile. This amino acid is shown to be a direct biosynthetic precursor to paraherquamide A by feeding and incorporation experiments in growing cultures of Penicillum fellutanum. Three tryptophan-containing dipeptides of L-beta -methylproline have been constructed: [(13)C(2)]-2-(l,1-dimethyl-2-propenyl)-L-tryptophanyl-3(S)-methyl-L-proline [(13)C(2)]-3(S)-methyl-L-prolyl-2-(l,1-dimethyl-2-propenyl)-L-tryptophan and [(13)C(2)]-cyclo-2-(l,1-dimethyl-2-propenyl)-L-tryptophan-3(S)-methyl-L-proline. [alpha-(15)N, 1-(13)C]-2-(1,1-Dimethyl-2-propenyl)-L-tryptophan was also prepared but none of these substances were found to serve as biosynthetic precursors to paraherquamide A. (C) 2001 Elsevier Science Ltd. All rights reserved.