10148-67-1

Basic information

• Product Name: (2S,3R)-2-AMINO-3-HYDROXY-PENTANOIC ACID
• Synonyms: (2S,3R)-2-AMINO-3-HYDROXY-PENTANOIC ACID;(2S,3R)-3-Hydroxynorvaline
• CAS NO: 10148-67-1
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 0
• Mol File: 10148-67-1.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3R)-2-AMINO-3-HYDROXY-PENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2-AMINO-3-HYDROXY-PENTANOIC ACID(10148-67-1)
• EPA Substance Registry System: (2S,3R)-2-AMINO-3-HYDROXY-PENTANOIC ACID(10148-67-1)

Safety Data

• Hazardous Substances Data: 10148-67-1(Hazardous Substances Data)

Usage

General Description

(2S,3R)-2-AMINO-3-HYDROXY-PENTANOIC ACID, also known as threonine, is an amino acid that plays a crucial role in the formation of proteins and the maintenance of overall health. It is classified as a non-essential amino acid, as the body can produce it on its own, but it is also obtained through dietary sources such as meat, dairy, and leafy green vegetables. Threonine is involved in the synthesis of elastin and collagen, which are essential for maintaining healthy skin and connective tissues. It also plays a role in the immune system, aiding in the production of antibodies and maintaining the proper balance of immune cells. Additionally, threonine is important for the metabolism of fats, and it has been shown to have potential benefits for the central nervous system and brain function.

Upstream product

• 2280-42-4 2-amino-3-hydroxy-valeric acid 
• 72-19-5 L-threonine 
• 123-38-6 propionaldehyde 
• 269064-89-3 1-[N,N-dibenzyl-(1S,2R)-1-amino-2-hydroxybutyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 
• 99092-44-1 (3R)-N-[(benzyloxy)carbonyl]-3-hydroxy-L-norvaline 
• 56-40-6 glycine 
• 1439368-22-5 ethyl 2-(tert-butoxycarbonylamino)-3-oxo-pentanoate 
• 13991-37-2 trans-2-pentenoic acid 
• 32817-15-5 copper(II) glycinate 

Downstream Products

• 62772-39-8 (+/-)-erythro-2-amino-3-hydroxy-valeric acid ethyl ester 
• 99092-44-1 (3R)-N-[(benzyloxy)carbonyl]-3-hydroxy-L-norvaline 
• 99092-43-0 2-Benzyloxycarbonylamino-3-hydroxy-pentanoic acid 

Relevant articles and documents

L -Threonine Transaldolase Activity Is Enabled by a Persistent Catalytic Intermediate

l-Threonine transaldolases (lTTAs) are a poorly characterized class of pyridoxal-5′-phosphate (PLP) dependent enzymes responsible for the biosynthesis of diverse β-hydroxy amino acids. Here, we study the catalytic mechanism of ObiH, an lTTA essential for biosynthesis of the β-lactone natural product obafluorin. Heterologously expressed ObiH purifies as a mixture of chemical states including a catalytically inactive form of the PLP cofactor. Photoexcitation of ObiH promotes the conversion of the inactive state of the enzyme to the active form. UV-vis spectroscopic analysis reveals that ObiH catalyzes the retro-aldol cleavage of l-threonine to form a remarkably persistent glycyl quinonoid intermediate, with a half-life of a??3 h. Protonation of this intermediate is kinetically disfavored, enabling on-cycle reactivity with aldehydes to form β-hydroxy amino acids. We demonstrate the synthetic potential of ObiH via the single step synthesis of (2S,3R)-β-hydroxyleucine. To further understand the structural features underpinning this desirable reactivity, we determined the crystal structure of ObiH bound to PLP as the Schiff's base at 1.66 ? resolution. This high-resolution model revealed a unique active site configuration wherein the evolutionarily conserved Asp that traditionally H-bonds to the cofactor is swapped for a neighboring Glu. Molecular dynamics simulations combined with mutagenesis studies indicate that a structural rearrangement is associated with l-threonine entry into the catalytic cycle. Together, these data explain the basis for the unique reactivity of lTTA enzymes and provide a foundation for future engineering and mechanistic analysis.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Compositions and methods for the treatment of bacterial infections include compounds containing a cyclic heptapeptide. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Compositions and methods for the treatment of bacterial infections include conjugates containing an Fc domain covalently linked to one or more monomers of cyclic heptapeptides or one or more dimers of cyclic heptapeptides. In particular, conjugates can be used in the treatment of bacterial infections caused by Gram-negative bacteria.