Phenylalanylserine methyl ester | 368424-85-5

• 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: Phenylalanylserine methyl ester
• 英文别名: Phe-Ser-OMe；methyl (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-hydroxypropanoate
• CAS: 368424-85-5
• 化学式: C₁₃H₁₈N₂O₄
• 分子量: 266.297
• InChiKey: RSDSJKVMUMGIEL-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Phenylalanylserine methyl ester 在 substituted Grubbs-type ruthenium carbene complex 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 methyl (2S)-3-hydroxy-2-[[(2S)-3-phenyl-2-[[(E)-4-[(2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]but-2-enoyl]amino]propanoyl]amino]propanoate
  参考文献：
  名称：

  Cross‐metathesis ofC‐Glycosides and Peptides

  摘要：

  Peptides bearing an acryloyl residue at their N-terminus were coupled with various C-glycosides in an equimolar ratio via cross-metathesis. The newly formed olefin was obtained with high E/Z selectivity in satisfying to high yields with low homodimerization of the starting materials. The posttranslational cross-metathesis approach was shown to be suitable for the combinatorial synthesis of a small library of C-glycopeptides.

  DOI：

  10.1080/00397910701481146
• 作为产物：
  描述：

  N-[(苄氧基)羰基]-L-苯丙氨酰-L-丝氨酸甲酯 在 palladium on activated charcoal 甲酸铵 作用下， 以 异丙醇 为溶剂， 反应 0.05h， 以95%的产率得到Phenylalanylserine methyl ester
  参考文献：
  名称：

  Rapid microwave-assisted deprotection of N-Cbz and N-Bn derivatives

  摘要：

  Catalytic-transfer hydrogenation in ifo-propanol under microwave irradiation has been performed to rapidly deprotect N-Cbz and N-Bn derivatives. The method is particularly suitable for the synthesis of short peptides and can also be carried out on supported molecules. The rapid cleavage of chiral molecules derived from (S)-1-phenylethylamine can be very useful for asymmetric synthesis of nitrogen containing compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00969-8

文献信息

• Tripodal Synthetic Peptide Bundles
  作者：Gunter Trojandt、Ulrike Herr、Kurt Polborn、Wolfgang Steglich

  DOI：10.1002/chem.19970030813

  日期：1997.8

  AbstractThe stereochemical course of the formation of the two diastereomers of trimethyl 2,2′,2″‐nitrilotris[2‐(benzoylamino)acetate], 2a and 2b, is described. The structures of both isomers were confirmed by X‐ray diffraction studies. Diastereomer 2b could be obtained in larger quantities by epimerisation of 2 a to 2 b with catalytical amounts of NaOMe. The (RRR/SSS)‐triester 2 b is a suitable template for the synthesis of tripodal peptide bundles. Saponification of 2 b yielded the C3‐symmetrical racemic triacid 4 b, which was coupled with amino acid methyl esters and dipeptide esters to give pseudo‐hexapeptides and pseudo‐nonapeptides, respectively. The resulting mixtures of diastereomers were easily separated by crystallisation. Their absolute configuration at the template unit (RRR or SSS) was established by means of the CD spectra. The pseudo‐hexapeptide (SSS)N(BzGly*ValOMe)3 (14) was saponified to yield the optically pure triacid (SSS)N(BzGly*ValOH)3 (23). Compound 23 is an ideally preorganised template for the production of longer tripodal peptides. This was illustrated by the synthesis of two pseudo‐pentadecapeptides. Peptide bundles with polar side chains (histidine and serine) or end groups (catechol or hydroxamate units) were synthesised by using the templates 4 b, 22 and 23 as anchors.
• Schwyzer,R.; Karlaganis,G., Justus Liebigs Annalen der Chemie, 1973, p. 1298 - 1309
  作者：Schwyzer,R.、Karlaganis,G.

  DOI：——

  日期：——
• Cross‐metathesis of<i>C</i>‐Glycosides and Peptides
  作者：Peter Brüchner、David Koch、Ulrike Voigtmann、Siegfried Blechert

  DOI：10.1080/00397910701481146

  日期：2007.8

  Peptides bearing an acryloyl residue at their N-terminus were coupled with various C-glycosides in an equimolar ratio via cross-metathesis. The newly formed olefin was obtained with high E/Z selectivity in satisfying to high yields with low homodimerization of the starting materials. The posttranslational cross-metathesis approach was shown to be suitable for the combinatorial synthesis of a small library of C-glycopeptides.
• Rapid microwave-assisted deprotection of N-Cbz and N-Bn derivatives
  作者：Maria Caterina Daga、Maurizio Taddei、Greta Varchi

  DOI：10.1016/s0040-4039(01)00969-8

  日期：2001.7

  Catalytic-transfer hydrogenation in ifo-propanol under microwave irradiation has been performed to rapidly deprotect N-Cbz and N-Bn derivatives. The method is particularly suitable for the synthesis of short peptides and can also be carried out on supported molecules. The rapid cleavage of chiral molecules derived from (S)-1-phenylethylamine can be very useful for asymmetric synthesis of nitrogen containing compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.