Efficient preparation of β-hydroxy aspartic acid and its derivatives

Long Liu, Bo Wang, Cheng Bi, Gang He, Gong Chen

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

We report an efficient and practical synthetic route to various properly-protected erythreo-β-OH-Asp compounds, which are key β-branched α-amino acid units in coralmycin A and other peptide natural products. Fmoc and cyclic ketal-protected erythreo-β-OH-Asp 7 is prepared from cheap chiral precursor L-diethyl tartrate in six steps without the need of column purification. The modified form of 7 serves as a versatile precursor to various β-alkoxyl analogs of erythreo-β-OH-Asp. In addition, we successfully performed a model study toward the total synthesis of coralmycin A, featuring a late stage installation of the side chain primary amide group of erythreo-β-OMe-Asn.

Original languageEnglish (US)
Pages (from-to)1113-1115
Number of pages3
JournalChinese Chemical Letters
Volume29
Issue number7
DOIs
StatePublished - Jul 1 2018

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Aspartic Acid
Derivatives
Distillation columns
Biological Products
Amides
Purification
Amino Acids
Peptides
hydroxide ion

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Liu, Long ; Wang, Bo ; Bi, Cheng ; He, Gang ; Chen, Gong. / Efficient preparation of β-hydroxy aspartic acid and its derivatives. In: Chinese Chemical Letters. 2018 ; Vol. 29, No. 7. pp. 1113-1115.
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Efficient preparation of β-hydroxy aspartic acid and its derivatives. / Liu, Long; Wang, Bo; Bi, Cheng; He, Gang; Chen, Gong.

In: Chinese Chemical Letters, Vol. 29, No. 7, 01.07.2018, p. 1113-1115.

Research output: Contribution to journalArticle

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AU - Bi, Cheng

AU - He, Gang

AU - Chen, Gong

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