cis-4-Hydroxy-L-proline
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cis-4-Hydroxy-L-proline
structure -
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CAS No:
618-27-9
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Formula:
C5H9NO3
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Chemical Name:
cis-4-Hydroxy-L-proline
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Synonyms:
L-Proline,4-hydroxy-,(4S)-;Proline,4-allo-hydroxy-,L-;L-Proline,4-hydroxy-,cis-;Proline,4-allo-hydroxy-;(4S)-4-Hydroxy-L-proline;cis-Hydroxyproline;allo-Hydroxy-L-proline;cis-4-Hydroxyproline;allo-L-Hydroxyproline;allo-4-Hydroxyproline;4-cis-Hydroxy-L-proline;L-Proline,allo-hydroxy-;L-allo-4-Hydroxyproline;L-Allohydroxyproline;L-allo-Hydroxyproline;(S)-allo-Hydroxyproline;(2S,4S)-4-Hydroxyproline;L-cis-4-Hydroxyproline;4(S)-Hydroxy-2(S)-pyrrolidinecarboxylic acid;cis-4-Hydroxy-L-proline;NSC 206274;(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid;H-Cis-Hyp-OH;(2S,4S)-4-Hydroxypyrrolidine-2-carboxylic acid;3398-20-7;30724-02-8
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CAS No:
Description
White to beige powder
Cis-4-hydroxy-L-proline is l-Proline in which a hydrogen at the 4-position of the pyrrolidine ring is substituted by a hydroxy group (S-configuration). It has a role as a metabolite. It is a non-proteinogenic L-alpha-amino acid and a 4-hydroxyproline. It is a tautomer of a cis-4-hydroxy-L-proline zwitterion.|A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.
Characteristics
69.6
-3.3
White to beige Powder
1.4±0.1 g/cm3
250.0-252.0 °C (decomp)
355.2°C at 760 mmHg
168.6±27.9 °C
1.540
soluble
Store at RT.
-59 º (c=2, H2O)
Safety Information
NONH for all modes of transport
3
36/37/38
24/25-36/37/39-27-26
Xi
Stable under normal temperatures and pressures.
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 5 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
cis-4-Hydroxy-L-proline Use and Manufacturing
The CBZ-cis-4-hydroxy-L-proline 28 was prepared as follows: 1.1 equivalents of (carbobenzyoxy)CBZ-chloride (Aldrich company) is added to 1.0 equivalents of cis-4-hydroxy-L-proline (Aldrich company) and allowed to stir for 12 hour at 25 C. in 0.10 M methylene chloride.To a solution of compound 1 (30g, 229mmol, eq) in Ethanol (300ml_) was added SOCI2 (16.7ml_, 229 mmol, 1 eq) drop wise at 0C. The mixture was brought to reflux for 16h. TLC analysis indicated formation of a less polar spot. The reaction mixture was cooled to 0C. A solid was filtered and dried under vacuum to give compound 2 (30 g, 83%) as an off white solid.
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.
L-Proline, 4-hydroxy-, (4S)-: ACTIVE
Computed Properties
Molecular Weight:131.13
XLogP3:-3.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:131.058243149
Monoisotopic Mass:131.058243149
Topological Polar Surface Area:69.6
Heavy Atom Count:9
Complexity:125
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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