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Cas Database

95464-27-0

95464-27-0

95464-27-0

Identification

Synonyms:1H-Pyrrole-1-hexanoicacid, a-amino-2-formyl-5-(hydroxymethyl)-,(?à)-

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Chemical Properties

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Relevant articles and documentsAll total 7 Articles be found

Transport of the Advanced Glycation End Products Alanylpyrraline and Pyrralylalanine by the Human Proton-Coupled Peptide Transporter hPEPT1

Stefanie, Geissler,Michael, Hellwig,Madlen, Zwarg,Fritz, Markwardt,Thomas, Henle,Matthias, Brandsch

, p. 2543 - 2547 (2010)

The glycation compound pyrraline, which originates from the advanced Maillard reaction, appears in urine after consumption of pyrraline-containlng food. We hypothesized that the absorption of pyrraline occurs In the form of dipeptides rather than the free amino acid. The human Intestinal peptide transporter hPEPT1 was transiently expressed in HeLa cells. In hPEPT1-transfected cells but not in cells transfected with empty vector, the uptake of [14C]glycylsarcosine was strongly inhibited by alanylpyrraline (Ala-Pyrr) and pyrralylalanine (Pyrr-Ala). Free pyrraline did not inhibit peptide uptake. In Xenopus laevis oocytes expressing human PEPT1, both Ala-Pyrr and Pyrr-Ala generated significant inward directed currents. In a third approach, uptake of the dipeptides into hPEPT1 -transfected HeLa cells was analyzed by HPLC. Ala-Pyrr and Pyrr-Ala were taken up by hPEPT1-expressing cells at a 4- to 7-fold higher rate than by HeLa cells transfected with the empty vector. We conclude that pyrraline containing dipeptides are transported by hPEPT1 in an electrogenlc manner into Intestinal cells. 2010 American Chemical Sudety.

Synthesis of monolysyl advanced glycation endproducts and their incorporation into collagen model peptides

Woods, Tom M.,Kamalov, Meder,Harris, Paul W. R.,Cooper, Garth J. S.,Brimble, Margaret

, p. 5740 - 5743 (2013/01/15)

The synthesis of advanced glycation endproducts (AGEs), CML, CEL, and pyrraline and their incorporation into collagen model peptides is reported. AGEs are modified amino acids that form on proteins such as collagen and are thought to play a significant role in the pathogenesis of many diseases, particularly diabetes. The synthesis and incorporation of these compounds into synthetic peptides is a key step in developing model systems with which to investigate AGE-modified proteins.

Synthesis of (±)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine. A biologically acitive Maillard reaction product derived from glucose and lysine

Miller,Olsson

, p. 717 - 723 (2007/10/02)

-

Process route upstream and downstream products

Process route

D-Glucose
2280-44-6

D-Glucose

L-Lysine hydrochloride
657-27-2,10098-89-2,26124-78-7

L-Lysine hydrochloride

2-furanoic acid
88-14-2

2-furanoic acid

5-hydroxymethyl-furan-2-carboxylic acid
6338-41-6

5-hydroxymethyl-furan-2-carboxylic acid

5-(3,4,5,6-tetrahydropyrid-3-ylidenemethyl)-2-furanmethanol

5-(3,4,5,6-tetrahydropyrid-3-ylidenemethyl)-2-furanmethanol

1-deoxy-1-(N<sup>6</sup>-lysino)-D-fructose
88125-05-7

1-deoxy-1-(N6-lysino)-D-fructose

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

2-deoxy-D-ribonolactone
34371-14-7

2-deoxy-D-ribonolactone

Conditions
Conditions Yield
In water; for 30h; Product distribution; Heating; pH 4.5;
5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde
67350-50-9

5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
2: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
3: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; barium hydroxide octahydrate; sodium t-butanolate; In methanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
2: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With barium hydroxide octahydrate; sodium t-butanolate; In water; N,N-dimethyl-formamide;
C<sub>27</sub>H<sub>28</sub>N<sub>2</sub>O<sub>6</sub>
1404451-32-6

C27H28N2O6

pyrraline
95464-27-0

pyrraline

Conditions
Conditions Yield
With piperidine; In dichloromethane; at 20 ℃; for 1.5h;
62%
(+/-)-N<sup>α</sup>-acetyl-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
103880-23-5

(+/-)-Nα-acetyl-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

Conditions
Conditions Yield
With barium hydroxide octahydrate; In water; for 24h; Heating;
65%
(+/-)-methyl α-acetamido-2-formyl-5-(hydroxymethyl)pyrrole-1-hexanoate
103880-22-4

(+/-)-methyl α-acetamido-2-formyl-5-(hydroxymethyl)pyrrole-1-hexanoate

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

Conditions
Conditions Yield
With barium hydroxide octahydrate; In water; for 24h; Heating;
59%
Multi-step reaction with 2 steps
1: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
2: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; barium hydroxide octahydrate; In methanol; water;
Boc-pyrraline
178180-79-5

Boc-pyrraline

pyrraline
95464-27-0

pyrraline

Conditions
Conditions Yield
With acetic acid; at 70 ℃;
119 mg
pyrrole-2,5-biscarboxaldehyde
39604-60-9

pyrrole-2,5-biscarboxaldehyde

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
2: 70 percent / sodium borohydride / methanol
3: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
4: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; In methanol; water; acetonitrile;
Multi-step reaction with 3 steps
1: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
2: 70 percent / sodium borohydride / methanol
3: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; In methanol; water; acetonitrile;
Multi-step reaction with 5 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
3: 70 percent / sodium borohydride / methanol
4: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
5: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
Multi-step reaction with 4 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
3: 70 percent / sodium borohydride / methanol
4: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
Multi-step reaction with 5 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: 71 percent / sodium borohydride / methanol / 0.25 h
3: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
4: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
5: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
Multi-step reaction with 4 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: 71 percent / sodium borohydride / methanol / 0.25 h
3: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
4: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
dimethyl acetamido-(4-brombutyl)malonate
103880-14-4

dimethyl acetamido-(4-brombutyl)malonate

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
3: 70 percent / sodium borohydride / methanol
4: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
5: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
Multi-step reaction with 4 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
3: 70 percent / sodium borohydride / methanol
4: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
Multi-step reaction with 5 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: 71 percent / sodium borohydride / methanol / 0.25 h
3: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
4: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
5: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
Multi-step reaction with 4 steps
1: 75 percent / potassium carbonate / acetonitrile / 24 h / Heating
2: 71 percent / sodium borohydride / methanol / 0.25 h
3: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
4: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; dimethyl sulfoxide; acetonitrile;
Multi-step reaction with 5 steps
1: 35 percent / sulfuric acid (conc.) / acetic acid / Heating
2: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
3: 70 percent / sodium borohydride / methanol
4: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
5: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; sulfuric acid; potassium carbonate; In methanol; water; acetic acid; acetonitrile;
Multi-step reaction with 4 steps
1: 35 percent / sulfuric acid (conc.) / acetic acid / Heating
2: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
3: 70 percent / sodium borohydride / methanol
4: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; sulfuric acid; potassium carbonate; In methanol; water; acetic acid; acetonitrile;
Multi-step reaction with 4 steps
1: 35 percent / sulfuric acid (conc.) / acetic acid / Heating
2: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
3: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
4: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; barium hydroxide octahydrate; sulfuric acid; sodium t-butanolate; In methanol; water; acetic acid; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: 35 percent / sulfuric acid (conc.) / acetic acid / Heating
2: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
3: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With barium hydroxide octahydrate; sulfuric acid; sodium t-butanolate; In water; acetic acid; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1: lithium iodide dihydrate / acetonitrile / 48 h / Heating
2: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
3: 70 percent / sodium borohydride / methanol
4: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
5: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; acetonitrile;
Multi-step reaction with 4 steps
1: lithium iodide dihydrate / acetonitrile / 48 h / Heating
2: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
3: 70 percent / sodium borohydride / methanol
4: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; lithium iodide; In methanol; water; acetonitrile;
Multi-step reaction with 4 steps
1: lithium iodide dihydrate / acetonitrile / 48 h / Heating
2: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
3: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
4: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; barium hydroxide octahydrate; lithium iodide; sodium t-butanolate; In methanol; water; N,N-dimethyl-formamide; acetonitrile;
Multi-step reaction with 3 steps
1: lithium iodide dihydrate / acetonitrile / 48 h / Heating
2: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
3: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With barium hydroxide octahydrate; lithium iodide; sodium t-butanolate; In water; N,N-dimethyl-formamide; acetonitrile;
(+/-)-methyl 2-acetamido-6-bromohexanoate
103880-18-8

(+/-)-methyl 2-acetamido-6-bromohexanoate

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
2: 70 percent / sodium borohydride / methanol
3: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
4: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; In methanol; water; acetonitrile;
Multi-step reaction with 3 steps
1: 60 percent / potassium carbonate / acetonitrile / 16 h / Heating
2: 70 percent / sodium borohydride / methanol
3: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; potassium carbonate; In methanol; water; acetonitrile;
Multi-step reaction with 3 steps
1: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
2: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
3: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; barium hydroxide octahydrate; sodium t-butanolate; In methanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: 42 percent / sodium t-butoxide / dimethylformamide / 120 h
2: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With barium hydroxide octahydrate; sodium t-butanolate; In water; N,N-dimethyl-formamide;
dimethyl acetamido-<4-(2,5-diformyl-1-pyrrolyl)butyl>malonate
103880-19-9

dimethyl acetamido-<4-(2,5-diformyl-1-pyrrolyl)butyl>malonate

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine
95464-27-0

(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
2: 70 percent / sodium borohydride / methanol
3: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
4: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; lithium iodide; In methanol; water; dimethyl sulfoxide;
Multi-step reaction with 3 steps
1: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
2: 70 percent / sodium borohydride / methanol
3: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; lithium iodide; In methanol; water; dimethyl sulfoxide;
Multi-step reaction with 4 steps
1: 71 percent / sodium borohydride / methanol / 0.25 h
2: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
3: 78 percent / 1 M sodium hydroxide (aq.) / methanol / 1 h
4: 65 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium hydroxide; sodium tetrahydroborate; barium hydroxide octahydrate; lithium iodide; In methanol; water; dimethyl sulfoxide;
Multi-step reaction with 3 steps
1: 71 percent / sodium borohydride / methanol / 0.25 h
2: lithium iodide dihydrate / dimethylsulfoxide / 4 h / 120 °C
3: 59 percent / barium hydroxide octahydrate / H2O / 24 h / Heating
With sodium tetrahydroborate; barium hydroxide octahydrate; lithium iodide; In methanol; water; dimethyl sulfoxide;

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