CAS 618-27-9

cis-4-Hydroxy-L-proline

Description:

Cis-4-Hydroxy-L-proline is an amino acid derivative characterized by its unique structural features and stereochemistry. It is a cyclic compound, specifically a pyrrolidine derivative, with a hydroxyl group (-OH) attached to the fourth carbon of the proline backbone. This configuration contributes to its distinct properties, including its role in protein structure and function, particularly in collagen synthesis. The "cis" designation indicates that the hydroxyl group and the adjacent carbon chain are on the same side of the molecule, influencing its spatial arrangement and reactivity. Cis-4-Hydroxy-L-proline is known for its potential biological activities, including its involvement in the stabilization of collagen triple helices and its effects on cellular processes. It is soluble in water and exhibits a polar character due to the hydroxyl group, which can participate in hydrogen bonding. This compound is of interest in both biochemical research and pharmaceutical applications, particularly in the study of collagen-related disorders and the development of therapeutic agents.

Formula: C₅H₉NO₃

InChI: InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m0/s1

InChI key: InChIKey=PMMYEEVYMWASQN-IMJSIDKUSA-N

SMILES: C(O)(=O)[C@@H]1C[C@H](O)CN1

Synonyms:

• (2S,4S)-(-)-4-Hydroxy-2-pyrrolinecarboxylic acid
• (2S,4S)-4-Hydroxyproline
• (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid
• (4S)-4-Hydroxy-<span class="text-smallcaps">L</span>-proline
• (S)-allo-Hydroxyproline
• 4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acid
• 4-cis-Hydroxy-<span class="text-smallcaps">L</span>-proline
• <span class="text-smallcaps">L</span>-Allohydroxyproline
• <span class="text-smallcaps">L</span>-Proline, 4-hydroxy-, (4S)-
• <span class="text-smallcaps">L</span>-Proline, 4-hydroxy-, cis-
• <span class="text-smallcaps">L</span>-Proline, allo-hydroxy-
• <span class="text-smallcaps">L</span>-allo-4-Hydroxyproline
• <span class="text-smallcaps">L</span>-allo-Hydroxyproline
• <span class="text-smallcaps">L</span>-cis-4-Hydroxyproline
• H-Cis-Hyp-OH
• NSC 206274
• Proline, 4-allo-hydroxy-
• Proline, 4-allo-hydroxy-, <span class="text-smallcaps">L</span>-
• allo-4-Hydroxyproline
• allo-<span class="text-smallcaps">L</span>-Hydroxyproline
• allo-Hydroxy-<span class="text-smallcaps">L</span>-proline
• cis-4-Hydroxy-<span class="text-smallcaps">L</span>-proline
• cis-4-Hydroxyproline
• cis-Hydroxyproline
• L-Proline, 4-hydroxy-, cis-
• L-Proline, 4-hydroxy-, (4S)-
• (4S)-4-Hydroxy-L-proline

cis-4-Hydroxy-L-proline

CAS: 618-27-9

Formula: C₅H₉NO₃

Purity: >97.0%(T)(HPLC)

Color and Shape: White to Light yellow powder to crystaline

Molecular weight: 131.13

Ref: 3B-H1169

cis-4-Hydroxy-L-proline, 99%

CAS: 618-27-9

cis-4-Hydroxy-L-proline (CHP) is a proline analog that inhibits collagen synthesis and has been used as an anticancer compound. CHP blocked myotube formation and expression of sarcomeric myosin heavy chain in C2C12 murine skeletal muscle cells. CHP inhibited proliferation of murine Panc02 pancreatic

Formula: C₅H₉NO₃

Purity: 99%

Color and Shape: White to cream or pale yellow, Powder

Molecular weight: 131.13

Ref: 02-H27194

H-cis-Hyp-OH

CAS: 618-27-9

cis-L-Hydroxyproline inhibits the synthesis and extracellular deposition of collagen. The growth inhibition of pancreatic cancer cells induced by the Hyp isomer could be due to endoplasmatic reticulum stress.

Formula: C₅H₉NO₃

Purity: > 99%

Color and Shape: White Powder

Molecular weight: 131.13

Ref: 01-4011503

(2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid

CAS: 618-27-9

Formula: C₅H₉NO₃

Purity: 97%

Color and Shape: Solid

Molecular weight: 131.1299

Ref: IN-DA00372D

cis-4-Hydroxy-L-proline

CAS: 618-27-9

Formula: C₅H₉NO₃

Molecular weight: 131.13

Ref: 7W-GM8426

(2S,4S)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid

CAS: 618-27-9

(2S,4S)-(-)-4-Hydroxypyrrolidine-2-carboxylic acid

Formula: C₅H₉NO₃

Purity: 98%

Color and Shape: white solid

Molecular weight: 131.12985g/mol

Ref: 54-OR30769

cis-4-Hydroxy-L-proline

CAS: 618-27-9

cis-4-Hydroxy-L-proline

Purity: ≥98%

Molecular weight: 131.13g/mol

Ref: 54-BUP17950

cis-4-Hydroxy-L-proline-2,5,5-d3

CAS: 618-27-9

Purity: 97%

Molecular weight: 134.15

Ref: 3U-D7713

cis-4-Hydroxy-L-Proline

CAS: 618-27-9

Formula: C₅H₉NO₃

Molecular weight: 131.13

Ref: 4Z-P-166057

cis-4-Hydroxy-L-proline

CAS: 618-27-9

cis-4-Hydroxy-L-proline hinders collagen synthesis, extracellular deposition, and fibroblast growth.

Formula: C₅H₉NO₃

Purity: 99.88%

Color and Shape: Solid

Molecular weight: 131.13

Ref: TM-T37512

cis-4-Hydroxy-L-proline

CAS: 618-27-9

Applications Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.
References Lawrence, C., et al.: Biochem. J., 313, 185 (1996), Mori, H., et al.: J. Bacteriol., 179, 5677 (1997), Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (2001),

Formula: C₅H₉NO₃

Color and Shape: Off White Crystalline Powder

Molecular weight: 131.13

Ref: TR-H952375

cis-4-Hydroxy-L-proline

CAS: 618-27-9

Cis-4-Hydroxy-L-proline is a bound form of proline that is formed by the condensation of two molecules of glyoxylate. It is a basic structure and an intermediate in the synthesis of collagen, which is a protein found in connective tissue. Cis-4-Hydoxy-L-proline has been shown to be an active form of proline for the treatment of primary sclerosing cholangitis, as it can decrease bile acid levels. This compound has also been used as an analytical method for determining collagen content in biological samples. The polymerase chain reaction technique uses cis-4-Hydroxy-L-proline as a matrix effect to amplify DNA sequences. Cis-4-Hydroxy-L-proline has also been shown to have optimum concentrations at 3mM and 0.5mM in model systems.br>

Formula: C₅H₉NO₃

Purity: Min. 95%

Color and Shape: White Powder

Molecular weight: 131.13 g/mol

Ref: 3D-FH34725

(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid

CAS: 618-27-9

Formula: C₅H₉NO₃

Purity: 97%

Color and Shape: Solid, White powder

Molecular weight: 131.131

Ref: 10-F208781

cis-4-Hydroxy-L-proline-13C215N

Controlled Product

CAS: 618-27-9

Formula: C₂C₃H₉₁₅NO₃

Color and Shape: Neat

Molecular weight: 134.109

Ref: TR-H952371

cis-4-Hydroxy-L-proline-d3 (Major)

Controlled Product

CAS: 618-27-9

Stability Hygroscopic
Applications cis-4-Hydroxy-L-proline-d3 is deuterium labelled cis-4-Hydroxy-L-proline (H952375). Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of trans-4- and cis-3-hydroxy-L-proline.
References Lawrence, C., et al.: Biochem. J., 313, 185 (1996); Mori, H., et al.: J. Bacteriol., 179, 5677 (1997); Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (2001)

Formula: C₅D₃H₆NO₃

Color and Shape: Neat

Molecular weight: 134.15

Ref: TR-H952379