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Orientation of the peptide formation of n-phosphoryl amino acids in solution

Chinese Science Bulletin 2002年第22期47卷 1866-1870页

作者： CHEn Zhongzhou TOnG Yufeng CHEn Shuibing LI Yanmei CHEn YI ZHAO Yufen WAnG Jinfeng Bioorganic Phosphorus Chemistry Laboratory Department of ChemistrySchool of Life Science and EngineeringTsinghua UniversityBeijing 100084China national Laboratory of Biomacromolecules Center for Molecular BiologyInstitute of BiophysicsChinese Academy of SciencesBeijing 100101China

The peptide formation of n-phosphoryl aminoacids with amino acids proceeds in aqueous solution withoutany coupling reagents. After being separated in sephadex gelcolumn, the phosphoryl dipeptides were analyzed by theelectrospray ionization tandem mass spectrometry (ESIMS/MS). The result demonstrates that phosphoryl dipeptideswere datected in all the reaction systems. It is found tkat theformation of n-phosphoryl dipeptides is oriented: then-terminal amino acid residues of the n-phosphoryl dipep-tides are from n-phosphoryl amino acids, and the peptideelongation happened at the C-terminal. Only adipeptide, noβ-dipeptide, is formed in the n-phosphoryl dipeptides,showing that α-carboxylic group is activated selectively byn-pbosphorylation. Theoretical calculation shows that thepeptide formation of n-phosphoryl amino acids might hap-pen through a pentu-coordinate carboxylic-phosphoric in-termediate in solution. These results might give some clues tothe stlidy on the origin of proteins and protein

关键词： n-phosphoryl amino acids orientation of peptide formation solution n-phosphoryl dipeptides.

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The Regulation Effect of phosphoryl Group on Amino Acid Side Chain

引用

Science China Chemistry 1993年第12期36卷 1451-1458页

作者：赵玉芬李艳梅尹应武李援朝 Department of Chemistry Tsinghua Uniuersity Beijing 100084 PRC

The amino acids’ side chains act as the relay device to modulate the chemical reactivity of the n-phosphoryl amino acids. The n-dialkyl phosphoryl cysteine is stable, but the n-dialkyl phosphoryl serine or threoine was converted into many kinds of products at 40℃. The n-dialkyl phosphoryl gltamic acid is a stable compound, while the n-dislkyl phosphoryl aspartic acid was transferred into the peptides, esters and the phosphoryl ester-exchanged products under mild conditions. The n-dialkyl phosphoryl histidine has the similar reactivity through the co-participation of the side chain, carboxyl and phosphoryl groups. A hexacoordinate phosphorus was proposed to account for this differentiation and promotion effect.

关键词： n-phosphoryl amino acid amino acid aide chain’s regulation effect partieipation of phosphoryl group hexaeoordinate phosphorus.

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