Cis-4-Hydroxy-D-proline (2584-71-6)

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Description

Cis-4-Hydroxy-D-proline (2584-71-6) video

Cis-4-Hydroxy-D-proline belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from a reaction of proline at the amino group or the carboxyl group, or from the replacement of any hydrogen of glycine by a heteroatom. cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase.

Cis-4-Hydroxy-D-proline synonyms: NSC 524341;D-cis-Hyp-OH;H-D-CIS-HYP-OH;D-CIS-HYDROXYPROLINE;CIS-D-HYDROXYPROLINE;4β-Hydroxy-D-proline;cis-4-Hydroxy-D-prol;D-ALLO-HYDROXYPROLINE;D-CIS-4-HYDROXYPROLINE;CIS-D-4-HYDROXYPROLINE.D-proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (R-configuration).

Epimerization of trans-4-hydroxy-l-proline to cis-4-hydroxy-d-proline during acid hydrolysis of collagen:

  1. Trans-4-Hydroxy-l-proline is epimerized to cis-4-hydroxy-d-proline under the conditions generally used for the hydrolysis of proteins for analyses of amino acids.
  2. The cis epimer elutes from a column of UR-30 resin on a Beckman amino acid analyzer at the same time as threonine and hence would be undetected.
  3. About 8% of the trans-4-hydroxy-l-proline in collagen can be epimerized to cis-4-hydroxy-d-proline in the hydrolysis of collagen with 6 N HCl at 110° for 72 hr.

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cis-4-Hydroxy-D-proline (2584-71-6) Specifications

CAS 2584-71-6
CAS Min % 95%
CAS Max % 100%
MDL Number MFCD00005252
InChI Key PMMYEEVYMWASQN-QWWZWVQMSA-N
Chemical Name or Material cis-4-Hydroxy-D-proline
Infrared Spectrum Authentic
Physical Form Powder
Packaging Glass bottle
Molecular Formula C5H9NO3
Molecular Weight (g/mol) 131.13
SMILES O[[email protected]]1CN[[email protected]](C1)C(O)=O
Color WHITE TO OFF-WHITE
Melting Point 243 °C
Assay 98%

cis-4-Hydroxy-D-proline (2584-71-6) Safety and HandlingAPICMO hazard icons

(2584-71-6) GHS H Statement

  • Not a hazardous substance or mixture.

cis-4-Hydroxy-D-proline GHS P Statement

  • Not a hazardous substance or mixture.
  • If inhaled:If breathed in, move person into fresh air. If not breathing, give artificial respirationSigma
  • In case of skin contact:Wash off with soap and plenty of water.
  • In case of eye contact:Flush eyes with water as a precaution.
  • If swallowed: Never give anything by mouth to an unconscious person. Rinse mouth with water

WARNING: The information provided on this web site was developed in compliance with European Union (EU) regulations and is correct to the best of our knowledge, information and belief at the date of its publication. The information given is designed only as a guide for safe handling and use. It is not to be considered as either a warranty or quality specification.

cis-4-Hydroxy-D-proline (2584-71-6) Articles

Epimerization of trans-4-hydroxy-l-proline to cis-4-hydroxy-d-proline during acid hydrolysis of collagen

A procedure is described whereby the primary amino acids in hydrolyzates are deaminated with nitrous acid and removed so that the amounts of trans-4-hydroxyproline, cis-4-hydroxyproline, and proline can be determined without changing the temperature of the column of UR-30 resin on the Beckman amino acid analyzer.

Dental Research Institute, The University of Michigan, Ann Arbor, Michigan 48104, USA

Characterization of cis-4-hydroxy-D-proline dehydrogenase from Sinorhizobium meliloti

The hypO gene from Sinorhizobium meliloti, located within the trans-4-hydroxy-L-proline metabolic gene cluster, was first successfully expressed in the host Pseudomonas putida. Purified HypO protein functioned as a FAD-containing cis-4-hydroxy-D-proline dehydrogenase with a homomeric structure.

Bioscience, Biotechnology and Biochemistry 2018 vol. 82 # 1 p. 110 – 113

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