cas 32926-43-5, N-Boc-N'-trityl-L-histidine | Articles data ｜lookchem

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32926-43-5

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Synthesis and evaluation of deglycobleomycin A2 analogues containing a tertiary N-methyl amide and simple ester replacement for the L-histidine secondary amide: Direct functional characterization of the requirement for secondary amide metal complexation
The synthesis and comparative examination of 3-5, analogues of deglycobleomycin A2 (2) which address the inferred importance of the L-histidine secondary amide directly, are detailed. The agent 3 lacks only the L-histidine β-hydroxy group of deglycobleomycin A2 and the corresponding agents 4 and 5 incorporate a tertiary N-methyl amide and simple ester in place of the L-histidine secondary amide. The DNA cleavage properties of 3 proved essentially indistinguishable from those of deglycobleomycin A2 (2) confirming that the distinctions between bleomycin A2 (1) and deglycobleomycin (2) are due to the removal of the disaccharide and not the introduction of the L-histidine free β-hydroxy group. The agents 4 and 5 containing a tertiary N-methyl amide and ester in place of the L-histidine secondary amide were found to cleave duplex DNA but to do so in a nonsequence selective fashion with a substantially reduced efficiency and a diminished double to single strand cleavage ratio that are only slightly greater than that of free iron itself. These latter observations establish the functional requirement for the L-histidine secondary amide and are consistent with the proposals that the L-histidine deprotonated secondary amide is required for functional metal chelation and activity.
Boger, Dale L.,Teramoto, Shuji,Cai, Hui
p. 179 - 193
(2007/10/03)

IMPROVED METHODS OF OBTAINING Nim-TRITYL-SUBSTITUTED HISTIDINE DERIVATIVES
Two variants are proposed for the synthesis of Nα-Boc-Nim-tritylhistidiine.The first variant starts from Nα,Nim-di-Boc-histidine, from which the Nim-Boc group is removed with hydrazine hydrate.The Nα-Boc-histidine formed is esterified with chlorotrimethylsilane, tritylated in the imidazole group, and, after the elimination of the trimethylsilyl protection from the carboxyl group, Nα-Boc-Nim-tritylglycine is obtained with a yield of 80percent.The second variant starts from Nα,Nim-ditritylhistidine, which, by treatment with hydrochloric acid in acetone and then with dilute ammonia, is converted into Nim- tritylhistidine.From this, by acylation with di-tert-butyl pyrocarbonate, Nα-Boc-Nim-tritylhistidine is obtained with a yield of 91percent.The acylation of Nim-tritylhistidine with other alkoxycarbonylating reagents leads to Nα-tert-amyl-, Nα-benzyl-, and Nα-4-methoxybenzyloxycarbonyl derivatives of Nim-tritylhistidine.
Pozdnev, V. F.
p. 322 - 327
(2007/10/02)

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Chemical Properties

Melting Point: ~130 °C (dec.)
Boiling Point: 667.5 °C at 760 mmHg
Flash Point:357.5 °C
Density: 1.16 g/cm³
Solubility:DMSO (Slightly), Methanol (Sparingly)
Storage Temp.:Store at 0°C
Vapor Pressure: 9.93E-19mmHg at 25°C
Refractive Index: 1.594
PKA: 3.17±0.10(Predicted)
BRN: 732035
PSA: 93.45000
LogP: 5.63460

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