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N-β-草酰-L-α,β-二氨基丙酸的化学合成及其神经毒性作用中的光学特异性

Chemical synthesis of N beta-oxalyl-L-alpha, beta-diaminopropionic acid and optical specificity in its neurotoxic action.

作者信息

Rao S L

出版信息

Biochemistry. 1975 Nov 18;14(23):5218-21. doi: 10.1021/bi00694a031.

DOI:10.1021/bi00694a031
PMID:1191635
Abstract

A practical procedure is described for the bulk synthesis of the neurotoxin N beta-oxalyl-L-alpha, beta-diaminopropionic acid (OA2pr3), a potential dicarboxylic amino acid antagonist of Lathyrus sativus seeds. L-Aspartic acid was reacted with sodium azide in 30% fuming sulfuric acid and L-alpha, beta-diaminopropionic acid hydrochloride (A2pr3-HCl) was isolated in yields greater than 75%. Potassium methyl oxalate was found to react selectively with the beta-amino group of S2pr3 resulting in near quantitative yields of OA2pr3. D-OA2pr3 has been made for the first time by this procedure. Unlike L-OA2pr3 the naturally occurring neurotoxin, D-OA2pr3, is not neuroactive even in high doses. The microsynthesis of L-[2,3-3H]A2pr3 from L-[2,3-3H]aspartic acid is also described, and the same procedure could also be used to prepare the neurotoxin with other labels. The availability of the neurotoxin in bulk and in labeled form should further experimental approaches to the understanding of its mechanism of action.

摘要

本文描述了一种用于大量合成神经毒素Nβ-草酰-L-α,β-二氨基丙酸（OA2pr3）的实用方法，OA2pr3是山黧豆种子中一种潜在的二羧酸氨基酸拮抗剂。L-天冬氨酸与叠氮化钠在30%发烟硫酸中反应，分离得到L-α,β-二氨基丙酸盐酸盐（A2pr3-HCl），产率大于75%。发现草酸甲酯钾能与S2pr3的β-氨基选择性反应，生成接近定量产率的OA2pr3。通过该方法首次制备了D-OA2pr3。与天然存在的神经毒素L-OA2pr3不同，即使高剂量的D-OA2pr3也没有神经活性。还描述了从L-[2,3-³H]天冬氨酸微量合成L-[2,3-³H]A2pr3的方法，同样的方法也可用于制备带有其他标记的神经毒素。大量且带标记形式的神经毒素的可得性应能推进对其作用机制的实验研究。

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Chemical synthesis of N beta-oxalyl-L-alpha, beta-diaminopropionic acid and optical specificity in its neurotoxic action.N-β-草酰-L-α,β-二氨基丙酸的化学合成及其神经毒性作用中的光学特异性
Biochemistry. 1975 Nov 18;14(23):5218-21. doi: 10.1021/bi00694a031.
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