Stereospecific synthesis of peptide analogs with allo-threonine and D-allo-threonine residues

Journal Article · Fri Mar 12 04:00:00 EST 1993 · Journal of Organic Chemistry; (United States)

DOI:https://doi.org/10.1021/jo00058a047· OSTI ID:6208308

Wipf, P; Miller, C P ^[1]

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1. Univ. of Pittsburgh, PA (United States)

In spite of their biological relevance, the use of D-allo-threonine has been considerably hampered by their high cost. Protocols for a de novo asymmetric synthesis or preparation from L-threonine are available but require multistep procedures and careful purification. A direct interconversion of peptide sequences with threonine, allo-threonine, and D-allo-threonine residues would greatly facilitate the study and application of these attractive structural variants. The authors have recently developed a mild and highly specific procedure for the preparation of peptide oxazolines and the authors now report an application of this methodology for the desired direct transformation of threonine and D-threonine peptide sequences into the corresponding allo-threonine and D-allo-threonine analogs. 16 refs., 3 figs.

• OSTI ID: 6208308
• Journal Information: Journal of Organic Chemistry; (United States), Journal Name: Journal of Organic Chemistry; (United States) Vol. 58:6; ISSN 0022-3263; ISSN JOCEAH
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
550200 -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
AMINO ACIDS
CARBOXYLIC ACIDS
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
DRUGS
HYDROXY ACIDS
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
ORGANIC ACIDS
ORGANIC COMPOUNDS
RESONANCE
STEREOCHEMISTRY
SYNTHESIS
THREONINE
YIELDS