Synonym
L-Erythrose; L-(+)-Erythrose;
IUPAC/Chemical Name
(2S,3S)-2,3,4-trihydroxybutanal
InChi Key
YTBSYETUWUMLBZ-DMTCNVIQSA-N
InChi Code
InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m1/s1
SMILES Code
O=C[C@H]([C@H](CO)O)O
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
An aldotetrose carbohydrate.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
120.10
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
TBD
1: Draskovits M, Stanetty C, Baxendale IR, Mihovilovic MD. Indium- and Zinc-Mediated Acyloxyallylation of Protected and Unprotected Aldotetroses-Revealing a Pronounced Diastereodivergence and a Fundamental Difference in the Performance of the Mediating Metal. J Org Chem. 2018 Mar 2;83(5):2647-2659. doi: 10.1021/acs.joc.7b03063. Epub 2018 Feb 9. PubMed PMID: 29369620; PubMed Central PMCID: PMC5838623.
2: Zou X, Lin J, Mao X, Zhao S, Ren Y. Biosynthesis of L-Erythrose by Assembly of Two Key Enzymes in Gluconobacter oxydans. J Agric Food Chem. 2017 Sep 6;65(35):7721-7725. doi: 10.1021/acs.jafc.7b02201. Epub 2017 Aug 24. PubMed PMID: 28707464.
3: Zweckmair T, Böhmdorfer S, Bogolitsyna A, Rosenau T, Potthast A, Novalin S. Accurate analysis of formose reaction products by LC-UV: an analytical challenge. J Chromatogr Sci. 2014 Feb;52(2):169-75. doi: 10.1093/chromsci/bmt004. Epub 2013 Feb 1. PubMed PMID: 23377653.
4: Jasiński M, Lentz D, Reissig HU. Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols. Beilstein J Org Chem. 2012;8:662-74. Epub 2012 Apr 30. PubMed PMID: 23015812; PubMed Central PMCID: PMC3388852.
5: Nishimura K, Harada T, Arita Y, Watanabe H, Iwabuki H, Terada A, Naganuma T, Uzuka Y. Identification of enzyme responsible for erythritol utilization and reaction product in yeast Lipomyces starkeyi. J Biosci Bioeng. 2006 Apr;101(4):303-8. PubMed PMID: 16716937.
6: Mizanur RM, Takeshita K, Moshino H, Takada G, Izumori K. Production of L-erythrose via L-erythrulose from erythritol using microbial and enzymatic reactions. J Biosci Bioeng. 2001;92(3):237-41. PubMed PMID: 16233090.
7: Argirov OK, Lin B, Olesen P, Ortwerth BJ. Isolation and characterization of a new advanced glycation endproduct of dehydroascorbic acid and lysine. Biochim Biophys Acta. 2003 Mar 17;1620(1-3):235-44. PubMed PMID: 12595094.
8: Ortwerth BJ, Speaker JA, Prabhakaram M, Lopez MG, Li EY, Feather MS. Ascorbic acid glycation: the reactions of L-threose in lens tissue. Exp Eye Res. 1994 Jun;58(6):665-74. PubMed PMID: 7925706.
9: Lerner LM. Some studies concerning the dimerization of 2,3-O-isopropylidene-L-erythrose. Carbohydr Res. 1990 Dec 15;208:273-5. PubMed PMID: 2150788.
10: Sperry JF, Robertson DC. Erythritol catabolism by Brucella abortus. J Bacteriol. 1975 Feb;121(2):619-30. PubMed PMID: 163226; PubMed Central PMCID: PMC245974.
11: FRIED J, WALZ DE, WINTERSTEINER O. Streptomycin; 4-desoxy-L-erythrose (threose) phenylosazone from streptobiosamine. J Am Chem Soc. 1946 Dec;68(12):2746. PubMed PMID: 20282418.
