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Structure

trans-3-Hydroxy-L-proline

CAS
4298-08-2
Catalog Number
ACM4298082
Category
Main Products
Molecular Weight
131.13
Molecular Formula
C5H9NO3

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  • Product Description
  • Case Study
  • Custom Reviews
  • Custom Q&A
  • Synthetic Use
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Specification

Synonyms
TRANS-3-HYDROXY-L-PROLINE;(2S,3S)-3-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;H-3-HYP-OH;L-3-TRANS-HYDROXYPROLINE;L-3-HYDROXYPROLINE;H-HYP(3)-OH;H-PRO(3-HYDROXY)-OH;2S,3S)-(-)-3-Hydroxy-2-pyrrolinecarboxylic acid
IUPAC Name
(2S,3S)-3-hydroxypyrrolidine-2-carboxylicacid
Canonical SMILES
C1CNC(C1O)C(=O)O
InChI Key
BJBUEDPLEOHJGE-IMJSIDKUSA-N
Boiling Point
355.2ºC at 760mmHg
Melting Point
235°C
Flash Point
168.6ºC
Density
1.395
Appearance
White to light beige powder
Exact Mass
131.05800
Safety Description
22-24/25

Multienzyme Cascade Reaction for the Synthesis of Trans-3-Hydroxy-L-Proline

The synthetic route of trans-3-hydroxy-L-proline involving larginine and 3-hydroxyarginine. Hara, Ryotaro, et al. Applied microbiology and biotechnology 100 (2016): 243-253.

Researchers have explored the four regio- and stereoisomeric variants of naturally occurring l-hydroxyproline as potential pharmaceutical precursors but no selective synthesis method for trans-3-hydroxy-l-proline has been created yet. The current study focuses on developing an innovative enzymatic asymmetric method for producing trans-3-hydroxy-l-proline.
The method consists of three steps involving L-arginine 3-hydroxylase (VioC), arginase, and ornithine cyclodeaminase (OCD) to achieve the asymmetric synthesis of (2S,3S)-3-hydroxyornithine and trans-3-Hyp within a short reaction timeframe. In the second step, arginase quantitatively converted (2S,3S)-3-hydroxyarginine into the expected hydroxyornithine. Nuclear magnetic resonance and chiral high-performance liquid chromatography confirmed that the compound's absolute configuration was (2S,3S)-3-hydroxyornithine. Finally, trans-3-hydroxy-l-proline was selectively synthesized from (2S,3S)-3-hydroxyornithine using ornithine cyclodeaminase in the last step. Consequently, this work successfully developed a streamlined three-reaction synthetic pathway to transform l-arginine into trans-3-hydroxy-l-proline, which outperforms traditional chemical synthesis in terms of selectivity and efficiency.

Synthesis, Properties and Applications of Hydroxyamino Acids Such as cis/trans-3-Hydroxy-L-Proline

Typical biocatalytic synthesis of hydroxylated L-amino acids including trans-3-hydroxy-l-proline (T3LHyp). Sun, D. Y., et al.IOP Conference Series: Earth and Environmental Science.188, 1.

Hydroxyamino acids have crucial functions in molecular biology and biotechnology through their antifungal, antibacterial, antiviral, and anticancer capabilities. Hydroxyamino acids also serve as components inside pharmaceutical intermediate production.
The properties of hydroxyproline
Hydroxyproline includes several isomers that exist in both cis and trans configurations like cis-3-hydroxy-L-proline (C3LHyp), trans-3-hydroxy-L-proline (T3LHyp), cis-4-hydroxy-L-proline (C4LHyp), and trans-4-hydroxy-L-proline (T4LHyp). Protein structures including collagen and peptide antibiotics and plant cell walls contain these forms while select isomers function as chiral components in pharmaceutical synthesis.
The properties of T3LHyp and C3LHyp
The most prevalent form of proline hydroxylation products within collagen is T3LHyp which forms predominantly through prolyl 3-hydroxylase activity. Conversely, C3LHyp has been recognized for its potential as a therapeutic agent in treating conditions like cancer and collagen disorders, establishing it as a key biologically active component in the synthesis of chiral drugs.
The synthesis of T3LHyp and C3LHyp
T3LHyp is mainly derived from a biosynthetic pathway that remains poorly understood, owing to limited research on proline trans-3-hydroxylase. In contrast, C3LHyp's production is more comprehensively documented, particularly through microbial processes. Johnston et al. transferred the L-proline cis-3-hydroxylase gene from Streptomyces sp. TH1 into E. coli to achieve high levels of gene expression. A fermentation system using L-proline as the substrate produced a C3LHyp yield of 99% after 60 hours of cultivation.

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