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441562

trans-1-Acetyl-4-hydroxy-L-proline

≥98%, for peptide synthesis

Synonym(s):

N-Acetyl-L-hydroxyproline

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About This Item

Empirical Formula (Hill Notation):
C7H11NO4
CAS Number:
33996-33-7
Molecular Weight:
173.17
Beilstein/REAXYS Number:
84043
EC Number:
251-780-6
MDL number:
MFCD00037339
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24867668
NACRES:
NA.22

Key Documents

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Product Name

trans-1-Acetyl-4-hydroxy-L-proline, ≥98%

assay

≥98%

form

powder

optical activity

[α]20/D −119°, c = 4 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

mp

132-133 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

CC(=O)N1C[C@H](O)C[C@H]1C(O)=O

InChI

1S/C7H11NO4/c1-4(9)8-3-5(10)2-6(8)7(11)12/h5-6,10H,2-3H2,1H3,(H,11,12)/t5-,6+/m1/s1

InChI key

BAPRUDZDYCKSOQ-RITPCOANSA-N

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This Item
96310H553415544
trans-1-Acetyl-4-hydroxy-L-proline ≥98%

Sigma-Aldrich

441562

trans-1-Acetyl-4-hydroxy-L-proline

Z-Hyp-OH ≥99.0% (T)

Sigma-Aldrich

96310

Z-Hyp-OH

trans-4-Hydroxy-L-proline BioReagent, suitable for cell culture, ≥98.5%

Sigma-Aldrich

H5534

trans-4-Hydroxy-L-proline

Boc-Hyp-OH ≥98.0% (TLC)

Sigma-Aldrich

15544

Boc-Hyp-OH

form

powder

form

powder

form

crystalline

form

-

assay

≥98%

assay

≥99.0% (T)

assay

≥98.5%

assay

≥98.0% (TLC)

optical activity

[α]20/D −119°, c = 4 in H2O

optical activity

[α]20/D −54±1°, c = 2% in ethanol

optical activity

-

optical activity

[α]20/D −53.5±2°, c = 1% in DMF

mp

132-133 °C (dec.) (lit.)

mp

104-107 °C

mp

273 °C (dec.) (lit.)

mp

123-127 °C (lit.)

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

reaction suitability

-

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Application

trans-1-Acetyl-4-hydroxy-L-proline can be used:
  • In the stereospecific synthesis of 4-fluoroglutamic acid.[1]
  • To synthesize molecular targets for von Hippel-Lindau (VHL) E3 ubiquitin ligase.[2]
  • As a precursor to synthesize pseudopoly(amino acids) such as poly(trans-4-hydroxy-4-acyl-L-proline ester)[3] and a biodegradable polymer, poly(lactic acid-glycolic acid-4-hydroxyproline).[4]

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ4845
MKCX8097
MKCW4937
MKCM2266
MKCM2330

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Stereospecific syntheses of all four stereoisomers of 4-fluoroglutamic acid.
Hudlicky M.
Journal of Fluorine Chemistry, 60(2-3), 193-210 (1993)
Pseudopoly (amino acids): A Study of the Synthesis and Characterization of Poly (trans-4-hydroxy-N-acyl-L-proline esters).
Kwon H Y and Langer R
Macromolecules, 22(8), 3250-3255 (1989)
Synthesis and characterization of a novel biodegradable polymer poly (lactic acid?glycolic acid?4?hydroxyproline).
Duan J, et al.
Journal of Applied Polymer Science, 103(6), 3585-3590 (2007)
Structure-guided design and optimization of small molecules targeting the protein?protein interaction between the von Hippel?Lindau (VHL) E3 ubiquitin ligase and the hypoxia inducible factor (HIF) alpha subunit with in vitro nanomolar affinities.
Galdeano C, et al.
Journal of Medicinal Chemistry, 57(20), 8657-8663 (2014)
J Ocaña et al.
Medicina cutanea ibero-latino-americana, 13(2), 157-166 (1985-01-01)
Approximately 30% of patients affected of PCT present scleroderma-like lesion of the skin. Two cases of PCT, presenting scleroderma-like lesions are reported. The patients were diabetic but not alcoholic and tolerate relatively well sunshine. Porphyrin elimination diminished with urine alkalinization
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