title: Trehalose and trehalose-based polymers for environmentally benign, biocompatible and bioactive materials.
abstract: Trehalose is a non-reducing disaccharide that is found in many organisms but not in mammals. This sugar plays important roles in cryptobiosis of selaginella mosses, tardigrades (water bears), and other animals which revive with water from a state of suspended animation induced by desiccation. The interesting properties of trehalose are due to its unique symmetrical low-energy structure, wherein two glucose units are bonded face-to-face by 1-->1-glucoside links. The Hayashibara Co. Ltd., is credited for developing an inexpensive, environmentally benign and industrial-scale process for the enzymatic conversion of alpha-1,4-linked polyhexoses to alpha,alpha-D-trehalose, which made it easy to explore novel food, industrial, and medicinal uses for trehalose and its derivatives. Trehalosechemistry is a relatively new and emerging field, and polymers of trehalose derivatives appear environmentally benign, biocompatible, and biodegradable. The discriminating properties of trehalose are attributed to its structure, symmetry, solubility, kinetic and thermodynamic stability and versatility. While syntheses of trehalose-based polymer networks can be straightforward, syntheses and characterization of well defined linear polymers with tailored properties using trehalose-based monomers is challenging, and typically involves protection and deprotection of hydroxyl groups to attain desired structural, morphological, biological, and physical and chemical properties in the resulting products. In this review, we will overview known literature on trehalose's fascinating involvement in cryptobiology; highlight its applications in many fields; and then discuss methods we used to prepare new trehalose-based monomers and polymers and explain their properties.
authors.affiliation: Department of Life and Environmental Sciences, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. teramoto-n@sea.it-chiba.ac.jp
authors.forename: Naozumi
authors.initials: N
authors.lastname: Teramoto
authors.forename: Navzer D
authors.initials: ND
authors.lastname: Sachinvala
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Shibata
mesh_terms: D001672:Biocompatible Materials / Q000737:chemistry; D002236:Carbohydrate Conformation; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry*; D014199:Trehalose / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use
chemical_list: D001672:Biocompatible Materials; D011108:Polymers; D014199:Trehalose
references.citation: Biophys J. 2001 Feb;80(2):931-8
references.pmid: 11159460
references.citation: J Biol Chem. 1968 Mar 10;243(5):957-61
references.pmid: 5640980
references.citation: Mol Microbiol. 2003 Feb;47(4):1163-81
references.pmid: 12581367
references.citation: Biophys J. 2004 Apr;86(4):2273-85
references.pmid: 15041666
references.citation: Trends Biotechnol. 2002 Oct;20(10):420-5
references.pmid: 12220904
references.citation: J Org Chem. 2002 May 3;67(9):3057-64
references.pmid: 11975567
references.citation: Biochim Biophys Acta. 1987 Jan 20;923(1):109-15
references.pmid: 2948571
references.citation: Cryobiology. 2001 Mar;42(2):79-87
references.pmid: 11448110
references.citation: J Biol Chem. 1962 Apr;237:1168-71
references.pmid: 13919530
references.citation: Adv Exp Med Biol. 2007;594:143-58
references.pmid: 17205682
references.citation: Biophys J. 2003 Nov;85(5):2830-44
references.pmid: 14581188
references.citation: J Bacteriol. 1971 Jul;107(1):217-22
references.pmid: 4327508
references.citation: Carbohydr Res. 2003 Apr 22;338(9):813-8
references.pmid: 12681904
references.citation: Vaccine. 2000 Dec 8;19(9-10):1239-45
references.pmid: 11137263
references.citation: Cryobiology. 2001 Sep;43(2):168-81
references.pmid: 11846471
references.citation: Biochim Biophys Acta. 1994 Jul 13;1193(1):143-50
references.pmid: 8038184
references.citation: J Biomol Struct Dyn. 1988 Jun;5(6):1163-71
references.pmid: 3271505
references.citation: Nutr Res. 2001 Jul;21(7):993-999
references.pmid: 11446983
references.citation: Planta. 1997 Mar;201(3):293-7
references.pmid: 19343407
references.citation: J Biol Chem. 1998 Dec 11;273(50):33311-9
references.pmid: 9837904
references.citation: Biophys Chem. 1997 Feb 28;64(1-3):25-43
references.pmid: 9127936
references.citation: Chem Biol. 2002 Dec;9(12):1337-46
references.pmid: 12498887
references.citation: Cryobiology. 2001 Sep;43(2):124-32
references.pmid: 11846467
references.citation: Nat Biotechnol. 2000 Feb;18(2):168-71
references.pmid: 10657122
references.citation: Biochim Biophys Acta. 1993 Mar 21;1156(3):263-6
references.pmid: 8461315
references.citation: J Bacteriol. 1992 Feb;174(3):889-98
references.pmid: 1310094
references.citation: Diabetes. 1997 Mar;46(3):519-23
references.pmid: 9032112
references.citation: Proc Natl Acad Sci U S A. 2003 May 27;100(11):6849-54
references.pmid: 12748379
references.citation: Biosci Biotechnol Biochem. 1995 Oct;59(10):1829-34
references.pmid: 8534970
references.citation: Philos Trans R Soc Lond B Biol Sci. 2003 Oct 29;358(1438):1755-71
references.pmid: 14561331
references.citation: Nephron. 1996;73(2):179-85
references.pmid: 8773341
references.citation: Mol Cell. 1998 Apr;1(5):639-48
references.pmid: 9660948
references.citation: Biosci Biotechnol Biochem. 1995 Dec;59(12):2215-8
references.pmid: 8611745
references.citation: Biotechnol Annu Rev. 1996;2:293-314
references.pmid: 9704101
references.citation: Cell Stress Chaperones. 1996 Jun;1(2):109-15
references.pmid: 9222596
references.citation: Neurobiol Dis. 2005 Oct;20(1):74-81
references.pmid: 16137568
references.citation: Biochim Biophys Acta. 2000 Feb 9;1476(2):377-81
references.pmid: 10669803
references.citation: Fertil Steril. 2002 Jan;77(1):152-8
references.pmid: 11779606
references.citation: Biomaterials. 2007 Jun;28(18):2885-98
references.pmid: 17367850
references.citation: Plant Mol Biol. 1995 Dec;29(5):1093-9
references.pmid: 8555452
references.citation: Plant Physiol. 2008 Jan;146(1):97-107
references.pmid: 17981987
references.citation: Adv Carbohydr Chem Biochem. 1974;30:227-56
references.pmid: 4377836
references.citation: Nat Biotechnol. 2000 Feb;18(2):163-7
references.pmid: 10657121
references.citation: Ann Thorac Surg. 1996 Apr;61(4):1099-105
references.pmid: 8607664
references.citation: J Biol Chem. 1958 Mar;231(1):259-75
references.pmid: 13538966
references.citation: Integr Comp Biol. 2002 Jul;42(3):497-503
references.pmid: 21708744
references.citation: Cryobiology. 1999 Sep;39(2):103-29
references.pmid: 10529304
references.citation: J Control Release. 2000 Jul 3;67(2-3):409-13
references.pmid: 10825571
references.citation: Arch Microbiol. 2000 Oct;174(4):217-24
references.pmid: 11081789
references.citation: Biochim Biophys Acta. 2006 Nov;1764(11):1677-87
references.pmid: 17046342
references.citation: Plant Biotechnol J. 2004 Jan;2(1):71-82
references.pmid: 17166144
references.citation: Biosci Biotechnol Biochem. 2001 Jun;65(6):1419-23
references.pmid: 11471747
references.citation: Glycobiology. 2003 Apr;13(4):17R-27R
references.pmid: 12626396
references.citation: Proc Natl Acad Sci U S A. 1968 Jul;60(3):1007-14
references.pmid: 5243919
references.citation: Proc Natl Acad Sci U S A. 1972 Sep;69(9):2373-6
references.pmid: 4341691
references.citation: Arch Biochem Biophys. 1960 Jun;88:339-43
references.pmid: 13825148
references.citation: Cryobiology. 2001 Sep;43(2):89-105
references.pmid: 11846464
references.citation: Cell Transplant. 2008;17(1-2):99-109
references.pmid: 18468240
references.citation: Drug Discov Today. 2003 Dec 15;8(24):1128-37
references.pmid: 14678739
references.citation: Biotechnol Bioeng. 1991 Mar 25;37(7):639-46
references.pmid: 18600655
references.citation: Gene. 1997 Nov 20;202(1-2):69-74
references.pmid: 9427547
references.citation: Biochem J. 1987 Feb 15;242(1):1-10
references.pmid: 2954537
references.citation: Prog Biophys Mol Biol. 2006 Oct;92(2):258-67
references.pmid: 16380155
references.citation: Res Microbiol. 1999 Oct;150(8):521-9
references.pmid: 10577485
references.citation: Vaccine. 2000 Oct 15;19(4-5):595-7
references.pmid: 11027826
references.citation: Science. 1959 Nov 13;130(3385):1343
references.pmid: 17753095
references.citation: Biochemistry. 2008 Feb 12;47(6):1789-96
references.pmid: 18205397
references.citation: Comp Biochem Physiol. 1965 Jan;14:135-43
references.pmid: 14288194
references.citation: Plant Physiol. 1989 Mar;89(3):977-81
references.pmid: 16666651
references.citation: Annu Rev Plant Biol. 2008;59:417-41
references.pmid: 18257709
references.citation: Cryobiology. 1982 Jun;19(3):306-16
references.pmid: 7105783
references.citation: Nature. 1964 Dec 19;204:1222
references.pmid: 14264398
references.citation: Annu Rev Physiol. 1998;60:73-103
references.pmid: 9558455
references.citation: Biotechnology (N Y). 1992 Sep;10(9):1007-11
references.pmid: 1369408
references.citation: Pediatr Infect Dis J. 1999 Oct;18(10):909-10
references.pmid: 10530589
references.citation: Genetics. 2004 Sep;168(1):21-33
references.pmid: 15454524
references.citation: Eur Biophys J. 1997;25(4):261-74
references.pmid: 21188574
references.citation: Arch Biochem Biophys. 2005 Dec 1;444(1):52-60
references.pmid: 16289020
references.citation: Plant Physiol. 1997 Jan;113(1):181-90
references.pmid: 9008394
references.citation: Biosci Biotechnol Biochem. 1996 Feb;60(2):263-6
references.pmid: 9063973
references.citation: Biochim Biophys Acta. 1984 Jan 11;769(1):141-50
references.pmid: 6691971
references.citation: Microbiol Immunol. 2007;51(6):581-92
references.pmid: 17579269
references.citation: Cell Transplant. 2006;15(10):911-9
references.pmid: 17299996
references.citation: Biotechnol Bioeng. 2004 Nov 5;88(3):299-312
references.pmid: 15486934
references.citation: Proc Natl Acad Sci U S A. 1998 Jan 20;95(2):520-4
references.pmid: 9435224
references.citation: Angew Chem Int Ed Engl. 2002 Jul 15;41(14):2596-9
references.pmid: 12203546
references.citation: J Am Chem Soc. 2006 Jun 28;128(25):8176-84
references.pmid: 16787082
references.citation: Dev Biol Stand. 1996;87:193-9
references.pmid: 8854017
references.citation: Org Biomol Chem. 2006 Feb 21;4(4):702-6
references.pmid: 16467944
references.citation: Yonsei Med J. 2004 Dec 31;45(6):1107-14
references.pmid: 15627304
references.citation: Comp Biochem Physiol A Mol Integr Physiol. 2002 Mar;131(3):505-13
references.pmid: 11867276
references.citation: Proc R Soc Lond B Biol Sci. 1959 Mar 17;150(939):149-91
references.pmid: 13633975
references.citation: Biochemistry. 1982 Dec 7;21(25):6536-44
references.pmid: 7150574
references.citation: Biochem Biophys Res Commun. 2007 Mar 23;354(4):899-905
references.pmid: 17266925
references.citation: J Gen Physiol. 1957 Jul 20;40(6):833-47
references.pmid: 13439163
references.citation: Biosci Biotechnol Biochem. 1996 Jan;60(5):835-9
references.pmid: 27281143
references.citation: Appl Biochem Biotechnol. 1990 Feb;23(2):155-70
references.pmid: 2139771
references.citation: Nat Med. 2004 Feb;10(2):148-54
references.pmid: 14730359
references.citation: Biophys J. 1996 Apr;70(4):1769-76
references.pmid: 8785336
references.citation: Clin Chem. 2000 May;46(5):636-43
references.pmid: 10794745
references.citation: Microb Ecol. 2004 Feb;47(2):164-74
references.pmid: 14749909
references.citation: J Exp Biol. 2004 Apr;207(Pt 10):1607-13
references.pmid: 15073193
references.citation: Biochim Biophys Acta. 1998 Sep 16;1425(1):245-54
references.pmid: 9813351
references.citation: Exp Cell Res. 1994 May;212(1):77-83
references.pmid: 8174644
references.citation: J Bacteriol. 1968 Jul;96(1):105-10
references.pmid: 5663563
references.citation: J Chem Phys. 2005 May 1;122(17):174513
references.pmid: 15910051
references.citation: Adv Carbohydr Chem. 1963;18:201-25
references.pmid: 14272317
references.citation: Science. 1993 May 14;260(5110):920-6
references.pmid: 8493529
references.citation: Stem Cells Dev. 2004 Jun;13(3):295-305
references.pmid: 15186725
references.citation: J Pharm Sci. 2002 Feb;91(2):388-95
references.pmid: 11835198
references.citation: Biochim Biophys Acta. 1976 May 21;433(3):469-81
references.pmid: 1276190
references.citation: Aesthet Surg J. 2005 Mar-Apr;25(2):126-31
references.pmid: 19338802
references.citation: Biochim Biophys Acta. 1983 Dec 12;749(2):133-42
references.pmid: 6652094
references.citation: Arch Biochem Biophys. 1981 Sep;210(2):517-24
references.pmid: 7305341
references.citation: Arch Biochem Biophys. 1998 Dec 1;360(1):10-4
references.pmid: 9826423
references.citation: Arch Biochem Biophys. 1984 Jul;232(1):400-7
references.pmid: 6742860
references.citation: Hum Mol Genet. 2006 Jan 1;15(1):23-31
references.pmid: 16311254
references.citation: Biophys J. 1996 Oct;71(4):2087-93
references.pmid: 8889183
references.citation: Biochemistry. 1979 Nov 13;18(23):5191-6
references.pmid: 497177
references.citation: Appl Environ Microbiol. 1995 Oct;61(10):3592-7
references.pmid: 7486995
references.citation: FEBS Lett. 2004 Apr 23;564(1-2):121-5
references.pmid: 15094052
references.citation: Biotechnol Bioeng. 1999 Dec 5;65(5):572-8
references.pmid: 10516583
references.citation: Biochem J. 1956 Feb;62(2):177-83
references.pmid: 13293170
references.citation: Prog Nucleic Acid Res Mol Biol. 1998;58:197-237
references.pmid: 9308367
references.citation: Eur J Biochem. 1993 Mar 1;212(2):315-23
references.pmid: 8444170
references.citation: Eur J Biochem. 1992 Nov 1;209(3):951-9
references.pmid: 1425702
references.citation: Biotechnol Bioeng. 2000 Oct 20;70(2):208-16
references.pmid: 10972932
references.citation: Scand J Gastroenterol Suppl. 1996;216:111-21
references.pmid: 8726284
references.citation: Protein Sci. 2006 Jul;15(7):1735-44
references.pmid: 16815921
references.citation: J Biol Chem. 1967 Feb 10;242(3):403-6
references.pmid: 6022837
references.citation: Nat Med. 2004 Jul;10 Suppl:S10-7
references.pmid: 15272267
references.citation: Biosci Biotechnol Biochem. 1996 Mar;60(3):546-50
references.pmid: 8901122
references.citation: Biosci Biotechnol Biochem. 1995 Dec;59(12):2210-4
references.pmid: 8611744
references.citation: Biochim Biophys Acta. 1996 Feb 9;1289(1):10-3
references.pmid: 8605217
references.citation: J Vet Med B Infect Dis Vet Public Health. 2006 Sep;53(7):299-305
references.pmid: 16930272
references.citation: J Hematother Stem Cell Res. 2001 Oct;10(5):709-18
references.pmid: 11672518
references.citation: Mol Microbiol. 1993 Apr;8(2):205-10
references.pmid: 8391102
references.citation: J Pharm Sci. 2001 Mar;90(3):310-21
references.pmid: 11170024
references.citation: Carbohydr Res. 2007 Oct 15;342(14):2014-30
references.pmid: 17559818
references.citation: Lancet. 1990 Oct 6;336(8719):854-5
references.pmid: 1976884
references.citation: Integr Comp Biol. 2005 Nov;45(5):715-24
references.pmid: 21676822
references.citation: Cell Death Differ. 2007 Mar;14(3):616-24
references.pmid: 16977331
references.citation: Reprod Biomed Online. 2005 Dec;11(6):733-9
references.pmid: 16417738
references.citation: Br J Ophthalmol. 2001 May;85(5):610-2
references.pmid: 11316726
references.citation: Int J Parasitol. 1997 Feb;27(2):215-29
references.pmid: 9088992
references.citation: Thorac Cardiovasc Surg. 1993 Feb;41(1):59-63
references.pmid: 8367858
references.citation: Arch Biochem Biophys. 1985 Oct;242(1):240-7
references.pmid: 4051504
references.citation: Science. 1984 Feb 17;223(4637):701-3
references.pmid: 17841031
references.citation: Comp Biochem Physiol B Biochem Mol Biol. 2007 Apr;146(4):456-60
references.pmid: 17261378
references.citation: Liver Transpl. 2007 Jan;13(1):38-45
references.pmid: 17154395
references.citation: Proteins. 2004 Apr 1;55(1):177-86
references.pmid: 14997551
references.citation: Ophthalmology. 2002 Nov;109(11):2024-9
references.pmid: 12414409
references.citation: Cryobiology. 2001 May;42(3):207-17
references.pmid: 11578120
references.citation: Comp Biochem Physiol B Biochem Mol Biol. 2001 Apr;128(4):613-24
references.pmid: 11290443
references.citation: Plant Mol Biol. 2007 Jul;64(4):371-86
references.pmid: 17453154