Benesch R E, Yung S, Suzuki T, Bauer C, Benesch R
Proc Natl Acad Sci U S A. 1973 Sep;70(9):2595-9. doi: 10.1073/pnas.70.9.2595.
Bifunctional pyridoxal derivatives with a charged side chain in the 5' position react specifically with the N-terminal valine residues of hemoglobin. Three of these compounds, which have only a single negative charge in the side chain, are highly selective for the alpha-chain N-terminal residues in the oxy conformation while pyridoxal phosphate, with two negative charges, reacts specifically with the beta N-terminal in deoxyhemoglobin. Schiff's base formation, therefore, results in decreased oxygen affinity with pyridoxal phosphate but increased oxygen affinity with the other three compounds. Reduction with sodium borohydride leads to irreversible coupling at either end of the molecule, and preparation and properties of such derivatives are described.
在5'位置带有带电侧链的双功能吡哆醛衍生物能与血红蛋白的N端缬氨酸残基发生特异性反应。其中三种化合物在侧链上仅带有一个负电荷,对氧合构象中的α链N端残基具有高度选择性,而带有两个负电荷的磷酸吡哆醛则与脱氧血红蛋白中的β N端发生特异性反应。因此,席夫碱的形成导致磷酸吡哆醛使氧亲和力降低,而其他三种化合物则使氧亲和力增加。用硼氢化钠还原会导致分子两端发生不可逆偶联,并描述了此类衍生物的制备方法和性质。